Artículo

De Leder Kremer, R.M.; Gallo-Rodriguez, C. "Naturally occurring monosaccharides: Properties and synthesis" (2004) Advances in Carbohydrate Chemistry and Biochemistry. 59:9-67
Estamos trabajando para incorporar este artículo al repositorio
Consulte el artículo en la página del editor
Consulte la política de Acceso Abierto del editor

Registro:

Documento: Artículo
Título:Naturally occurring monosaccharides: Properties and synthesis
Autor:De Leder Kremer, R.M.; Gallo-Rodriguez, C.
Filiación:CIHIDECAR, Depto. de Quím. Organ., Fac. Cie. Exact. Y Nat., Univ. B., Buenos Aires, Argentina
Palabras clave:galactose; hexose; monosaccharide; natural product; pentose; ribose; tetrose; triose; xylose; carbohydrate synthesis; priority journal; review; Biological Factors; Carbohydrate Conformation; Monosaccharides
Año:2004
Volumen:59
Página de inicio:9
Página de fin:67
DOI: http://dx.doi.org/10.1016/S0065-2318(04)59002-9
Título revista:Advances in Carbohydrate Chemistry and Biochemistry
Título revista abreviado:Adv. Carbohydr. Chem. Biochem.
ISSN:00652318
CODEN:ACBYA
CAS:galactose, 26566-61-0, 50855-33-9, 59-23-4; hexose, 93780-23-5; pentose, 53106-52-8; ribose, 34466-20-1, 50-69-1, 93781-19-2; xylose, 25990-60-7, 58-86-6; Biological Factors; Monosaccharides
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00652318_v59_n_p9_DeLederKremer

Referencias:

  • Schaffer, R., Occurrence, properties and preparation of naturally occurring monosaccharides (including 6-deoxy sugars) (1972) The Carbohydrates: Chemistry and Biochemistry, 2nd Edn., 1 A, pp. 69-111. , W. Pigman and D. Horton (Eds.), Academic Press, New York
  • Hanessian, S., Total synthesis of natural products: The 'Chiron' approach (1983) Organic Chemistry Series, 3. , J. E. Baldwin (Ed.), Pergamon Press, Oxford
  • Nicolaou, K.C., Mitchell, H.J., Adventures in carbohydrate chemistry: New synthetic technologies, chemical synthesis, molecular design, and chemical biology (2001) Angew. Chem. Int. Ed., 40, pp. 1576-1624
  • Hollingsworth, R.I., Wang, G., Toward a carbohydrate-based chemistry: Progress in the development of general-purpose chiral synthons from carbohydrates (2000) Chem. Rev., 100, pp. 4267-4282
  • Bednarski, M.D., Simon, E.S., Enzymes in carbohydrate synthesis (1991) ACS Symp. Ser., 466
  • Gijsen, H.J.M., Qiao, L., Fitz, W., Wong, C.-H., Recent advances in the chemoenzymatic synthesis of carbohydrates and carbohydrate mimetics (1996) Chem. Rev., 96, pp. 443-473
  • Duus J.Ø, Gotfredsen, C.H., Bock, K., Carbohydrate structural determination by NMR spectroscopy: Modern methods and limitations (2000) Chem. Rev., 100, pp. 4589-4614
  • Chaplin, M.F., Gas-liquid chromatography (1986) Carbohydrate Analysis: A Practical Approach, pp. 23-33. , M. F. Chaplin and J. F. Kennedy (Eds.), IRL Press, Oxford
  • Fox, A., Morgan, S.L., Gilbart, J., Preparation of alditol acetates and their analysis by gas chromatography (GC) and mass spectrometry (1989) Analysis of Carbohydrates by GLC and MS, pp. 87-117. , C. J. Biermann and G. D. McGinnis (Eds.), CRC Press, Boca Raton
  • Lee, Y.C., High-performance anion-exchange chromatography for carbohydrate analysis (1990) Anal. Biochem., 189, pp. 151-162
  • Lehninger, A.L., Nelson, D.L., Cox, M.M., Glycolysis and the catabolism of hexoses (1993) Principles of Biochemistry, 2nd Edn., pp. 401-445. , Worth Publishers, New York
  • Best, L., Thornalley, P.J., Trioses and related substances: Tools for the study of pancreatic beta-cell function (1999) Biochem. Pharmacol., 57, pp. 583-588
  • Baer, E., Fischer, H.O.L., L(+)-Propylene glycol (1948) J. Am. Chem. Soc., 70, pp. 609-610
  • Perlin, A.S., Trioses. D-, L-, DL-Glyceraldehyde (1962) Methods Carbohydr. Chem., 1, pp. 61-63
  • Ballou, C.E., Fischer, H.O.L., The synthesis of d-glyceraldehyde-3-phosphate (1955) J. Am. Chem. Soc., 77, pp. 3329-3331
  • Betti, M., Pratesi, P., Über die optische Spaltung des racemischen Glycerinaldehyds (1934) Biochem. Z., 274, pp. 1-3
  • Strain, H.H., Dore, W.H., Polymerization of dihydroxyacetone (1934) J. Am. Chem. Soc., 56, pp. 2649-2650
  • Ballou, C.E., Fischer, H.O.L., The synthesis of dihydroxyacetone phosphate (1956) J. Am. Chem. Soc., 78, pp. 1659-1661
  • Overend, W.G., Stacey, M., Wiggins, L.F., Deoxy-sugars. Part IV. A synthesis of 2-deoxy-D-ribose from D-erythrose (1949) J. Chem. Soc., pp. 1358-1363
  • Perlin, A.S., Tetrose. D-Erythrose (1962) Methods Carbohydr. Chem., 1, pp. 64-66
  • Ballou, C.E., Fischer, H.O.L., MacDonald, D.L., The synthesis and properties of D-erythrose 4-phosphate (1955) J. Am. Chem. Soc., 77, pp. 5967-5970
  • McNeil, M.R., Wallner, S.J., Brennan, P.J., Demonstration that the galactosyl and arabinosyl residues in the cell-wall arabinogalactan of Mycobacterium leprae and Mycobacterium tuberculosis are furanoid (1987) Carbohydr. Res., 166, pp. 299-308
  • Lee, R.E., Brennan, P.J., Besra, G.S., Mycobacterial arabinan biosynthesis: The use of synthetic arabinoside acceptors in the development of an arabinosyl transfer assay (1997) Glycobiology, 7, pp. 1121-1128
  • Brennan, P.J., Nikaido, H., The envelope of mycobacteria (1995) Annu. Rev. Biochem., 64, pp. 29-63
  • Galbraith, L., Wilkinson, S.G., Structures of the O21 and O25 antigens of Stenotrophomonas maltophilia (2000) Carbohydr. Res., 323, pp. 98-102. , and references cited therein
  • Whistler, R.L., Bemiller, J.N., Pentoses. β-D-Arabinose (1962) Methods Carbohydr. Chem., 1, pp. 71-73
  • MacDonald, D.L., Methods Carbohydr. Chem., pp. 73-75
  • Odonmazig, P., Ebringerová, A., MacHová, E., Alföldi, J., Structural and molecular properties of the arabinogalactan isolated from Mongolian larchwood (Larix dahurica L.) (1994) Carbohydr. Res., 252, pp. 317-324
  • Karácsonyi, S., Pätoprstý, V., Kubacková, M., Structural study of arabinogalactan-proteins from Picea abies L. Krast (1998) Carbohydr. Res., 307, pp. 271-279
  • Ishii, T., Hiroi, T., Linkage of phenolic acids to cell-wall polysaccharide of bamboo shoot (1990) Carbohydr. Res., 206, pp. 297-310
  • Ishii, T., Hiroi, T., Structural characterization of feruloyl oligosaccharides from spinach-leaf cell walls (1993) Carbohydr. Res., 248, pp. 179-190
  • Dong, Q., Fang, J.N., Structural elucidation of a new arabinogalactan from the leaves of Nerium indicum (2001) Carbohydr. Res., 332, pp. 109-114
  • Hanniffy, O.M., Shashkov, A.S., Moran, A.P., Prendergast, M.M., Senchenkova, S.N., Knirel, Y.A., Savage, A.V., Chemical structure of a polysaccharide from Campylobacter jejuni 176.83 (serotype O:41) containing only furanose sugars (1999) Carbohydr. Res., 319, pp. 124-132
  • White, E.V., β-L-Arabinose (1962) Methods Carbohydr. Chem., 1, pp. 76-77
  • Hudson, C.S., Improvements in the preparation of L-arabinose from mesquite gum (1951) J. Am. Chem. Soc., 73, pp. 4038-4039
  • Khoo, K.-H., Suzuki, R., Dell, A., Morris, H.R., McNeil, M.R., Brennan, P.J., Besra, G.S., Chemistry of the lyxose-containing mycobacteriophage receptors of Mycobacterium phlei/Mycobacterium smegmatis (1996) Biochemistry, 35, pp. 11812-11819
  • Fletcher Jr., H.G., α-D-Lyxose (1962) Methods Carbohydr. Chem., 1, pp. 77-78
  • Ollis, W.D., Smith, C., Wright, D.E., Acidic hydrolysis products of flambamycin (1974) J. C. S. Chem. Commun., pp. 881-882
  • Whistler, R.L., Bemiller, J.M., α-L-Lyxose (1962) Methods Carbohydr. Chem., 1, pp. 79-80
  • Gil-Serrano, A.M., Rodriguez-Carvajal, M.A., Tejero-Mateo, P., Espartero, J.L., Thomas-Oates, J., Ruiz-Sainz, J.E., Buendia-Claveria, A.M., Structural determination of a 5-O-methyl-deaminated neuraminic acid (Kdn)-containing polysaccharide isolated from Sinorhizobium fredii (1998) Biochem. J., 334, pp. 585-594
  • Lindberg, B., Components of bacterial polysaccharides (1990) Adv. Carbohydr. Chem. Biochem., 48, pp. 279-318
  • MacLean, L.L., Perry, M.B., Structural characterization of the serotype O:5 O-polysaccharide antigen of the lipopolysaccharide of Escherichia coli O:5 (1997) Biochem. Cell Biol., 75, pp. 199-205
  • Winn, A.M., Wilkinson, S.G., Structure of the O16 antigen of Stenotrophomonas maltophilia (2001) Carbohydr. Res., 330, pp. 279-283
  • Helm, R.F., Huang, Z., Edwards, D., Leeson, H., Peery, W., Potts, M., Structural characterization of the released polysaccharide of desiccation-tolerant Nostoc commune DRH-1 (2000) J. Bacteriol., 182, pp. 974-982
  • Dephillipis, R., Vincenzini, M., Exocellular polysaccharides from cyanobacteria and their possible applications (1998) FEMS Microbiol. Rev., 22, pp. 151-175
  • Bates, F.J., D-Ribose (1942) Polarimetry, Saccharimetry, and the Sugars, Natl. Bur., pp. 476-479. , Standard Circular C440 United States Government Printing Office, Washington
  • Levene, P.A., Clark, E.P., D-Ribohexosaminic acids (1921) J. Biol. Chem., 46, pp. 19-33
  • Bredereck, H., Köthnig, M., Berger, E., Uber die D-Ribose (Darstellung einer krystallisierten Anhydroribose) (1940) Ber., 73, pp. 956-962
  • Jeanloz, R.W., Fletcher Jr., H.G., The chemistry of ribose (1951) Adv. Carbohydr. Chem., 6, pp. 135-174
  • Fry, S.C., Xyloglucan. A metabolically dynamic polysaccharide (1992) Trends Glycosci. Glycotechnology, 4, pp. 279-289
  • Wilson, I.B.H., Zeleny, R., Kolarich, D., Staudacher, E., Stroop, C.J.M., Kamerling, J.P., Altmann, F., Analysis of Asn-linked glycans from vegetable foodstuffs: Widespread occurrence of Lewis a, core α1,3-linked fucose and xylose substitutions (2001) Glycobiology, 11, pp. 261-274
  • Wilson, I.B.H., Altmann, F., Structural analysis of N-glycan of allergenic grass, ragweed and tree pollens: Core α1,3-linked fucose and xylose present in all pollens examined (1998) Glycoconj. J., 15, pp. 1055-1070
  • Richtmyer, N.K., The isolation of D-manno-heptulose, perseitol, D-glycero-D-manno- octulose, and other compounds from Pichi tops (Fabiana imbricata Ruiz & Pav.) (1970) Carbohydr. Res., 12, pp. 233-239
  • Whistler, R.L., Bemiller, J.N., α-D-Xylose (1962) Methods Carbohydr. Chem., 1, pp. 88-90
  • Biely, P., Vrsanská, M., Isolation of products of enzymic hydrolysis of xylan (1994) Methods Carbohydr. Chem., 10, p. 293
  • Prade, R.A., Xylanases: From biology to biotechnology (1996) Biotechnol. Genet. Eng. Rev., 13, pp. 101-131
  • Trahan, L., Xylitol: A review of its action on mutans streptococci and dental plaque-its clinical significance (1995) Int. Dent. J., 45, pp. 77-92
  • Senchenkova, S.N., Shashkov, A.S., Laux, P., Knirel, Y.A., Rudolph, K., The O-chain polysaccharide of the lipopolysaccharide of Xanthomonas campestris pv. begoniae GSPB 525 is a partially L-xylosylated L-rhamnan (1999) Carbohydr. Res., 319, pp. 148-153
  • Ness, R.K., α-L-Xylose (1962) Methods Carbohydr. Chem., 1, pp. 90-93
  • Glatthaar, C., Reichstein, T., D-Aldonose (D-Erythro-2-keto-pentose) (1935) Helv. Chim. Acta, 18, pp. 80-81
  • Adachi, O., Fujii, Y., Ano, Y., Moonmangmee, D., Toyama, H., Shinagawa, E., Theeragool, G., Matsushita, K., Membrane-bound sugar alcohol dehydrogenase in acetic acid bacteria catalyzes L-ribulose formation and NAD-dependent ribitol dehydrogenase is independent of the oxidative fermentation (2001) Biosci. Biotechnol. Biochem., 65, pp. 115-125
  • Quong, M.W., Miyada, C.G., Switchenko, A.C., Goodman, T.C., Identification, purification, and characterization of a D-arabinitol-specific dehydrogenase from Candida tropicalis (1993) Biochem. Biophys. Res. Commun., 196, pp. 1323-1329
  • Horecker, B.L., Hurwitz, J., Smyrniotis, P.Z., Xylulose 5-phosphate and the formation of sedoheptulose 7-phosphate with liver transketolase (1956) J. Am. Chem. Soc., 78, pp. 692-694
  • Wilkinson, S.G., Isolation of D-threo-pent-2-ulose from the lipopolysaccharide of Pseudomonas diminuta N.C.T.C. 8545 (1981) Carbohydr. Res., 98, pp. 247-252
  • Ovodov, Y.S., Gorshkova, R.P., Tomshich, S.V., Komandrova, N.A., Zubkov, V.A., Kalmykova, E.N., Isakov, V.V., Chemical and immunochemical studies on lipopolysaccharides of some Yersinia species. A review of some recent investigations (1992) J. Carbohydr. Chem., 11, pp. 21-35
  • Hough, L., Theobald, R.S., D-threo-Pentulose (1962) Methods Carbohydr. Chem., 1, pp. 94-98
  • Touster, O., D- and L-threo-Pentulose Methods Carbohydr. Chem., pp. 98-101
  • Barker, S.A., Enzymic interconversion of D-glucose and D-fructose, and of D-xylose and D-xylulose (1994) Methods Carbohydr. Chem., 10, pp. 241-248
  • Touster, O., Mayberry, R.H., McCormick, A.V., The conversion of 1-13C-D-glucuronolactone to 5- 13C-L-xylulose in a pentosuric human (1957) Biochim. Biophys. Acta, 25, pp. 196-198
  • Merimee, T.J., Misbin, R.I., Gold, L., Elevated L-xylulose concentrations in serum: A difference between type I and type II diabetes (1984) Metabolism, 33, pp. 82-84
  • Lane, A.B., On the nature of L-xylulose reductase deficiency in essential pentosuria (1985) Biochem. Genet., 23, pp. 61-72
  • Gorshkova, R.P., Isakov, V.V., Kalmykova, E.N., Ovodov, Y.S., Structural studies of O-specific polysaccharide chains of the lipopolysaccharide from Yersinia enterocolitica serovar O:10 (1995) Carbohydr. Res., 268, pp. 249-255
  • Von Vargha, L., Über die Konstitution des Monobenzal-D-sorbits. Eine Synthese del L-Xylose (1935) Ber., 68, pp. 18-24
  • Doten, R.C., Mortlock, R.P., Production of D- and L-xylulose by mutants of Klebsiella pneumoniae and Erwinia uredovora (1985) Appl. Environ. Microbiol., 49, pp. 158-162
  • Christensen, J., Jaroszewski, J.W., Natural glycosides containing allopyranose from the passion fruit plant and circular dicroism of benzaldehyde cyanohydrin glycosides (2001) Org. Lett., 3, pp. 2193-2195
  • Jensen, S.R., Nielsen, B.J., Norn, V., Iridoids from Viburnum dilatatum (1985) Phytochemistry, 24, pp. 487-489
  • Hase, T., Iwagawa, T., Dave, M.N., Three iridoid glycosides from Viburnum furcatum betulifolium (1985) Phytochemistry, 24, pp. 1323-1327
  • Toyota, M., Saito, T., Asakawa, Y., A phenethyl glycoside from Conocephalum conicum (1996) Phytochemistry, 43, pp. 1087-1088
  • Jensen, S.R., Caffeoyl phenylethanoid glycosides in Sanango racemosum and in the Gesneriaceae (1996) Phytochemistry, 43, pp. 777-783
  • Perold, G.W., Beylis, P., Howard, A.S., Metabolites of Proteaceae. Part VIII. The occurrence of (+)-D-allose in Nature: Rubropilosin and pilorubrosin from Protea rubropilosa Beard (1973) J. Chem. Soc. Perkin Trans., 1, pp. 643-648
  • Songqing, L., Zhuoyin, X., Rui, F., A flavonol glycoside from Drynaria propinqua (1994) Phytochemistry, 35, pp. 1595-1596
  • Hasan, A., Farman, M., Ahmed, I., Flavonoid glycosides from Indigofela hebepetala Phytochemistry, 35, pp. 275-276
  • Murakami, T., Satake, T., Ninomiya, K., Iida, H., Yamauchi, K., Tanaka, N., Saiki, Y., Chen, C.-M., Pterosin-derivative aus der Familie Pteridaceae (1980) Phytochemistry, 19, pp. 1743-1746
  • Redgwell, R.J., Beever, R.E., Bieleski, R.L., Laracy, E.P., Benn, M.H., Isolation and characterization of (E)-4-hydroxy-2-(hydroxymethy)but-2- enyl β-D-allopyranoside, the major soluble carbohydrate in leaves of the fern Cardiomanes reniforme (1990) Carbohydr. Res., 198, pp. 39-48
  • Humoller, F.L., β-D-Allose (1962) Methods Carbohydr. Chem., 1, pp. 102-104
  • Baker, D.C., Horton, D., Tindall Jr., C.G., (1972) Carbohydr. Res., 24, pp. 192-197
  • Stack, R.J., Identification of L-altrose in the extracellular polysaccharide from Butyrivibrio fibrisolvens strain CF3 (1987) FEMS Microbiol. Lett., 48, pp. 83-87
  • Ferreira, F., Kenne, L., Cotta, M.A., Stack, R.J., Structural studies of the extracellular polysaccharide from Butyrivibrio fibrisolvens strain CF3 (1997) Carbohydr. Res., 301, pp. 193-203
  • Humoller, F.L., α-L-Altrose (1962) Methods Carbohydr. Chem., 1, pp. 114-116
  • Hung, S.-C., Wang, C.-C., Thopate, S.R., Efficient synthesis of L-altrose and L-mannose (2000) Tetrahedron Lett., 41, pp. 3119-3122
  • Painter, T.J., Algal Polysaccharides (1983) The Polysaccharides, 2, pp. 196-275. , G. O. Aspinall (Ed.), Academic Press, Orlando
  • Brown, R.J., Serro, R.F., Isolation and identification of O-α-D-galactopyranosyl-myo-inositol and of myo-inositol from juice of the sugar beet (Beta Vulgaris) (1953) J. Am. Chem. Soc., 75, pp. 1040-1042
  • Kabat, E.A., MacDonald, D.L., Ballou, C.E., Fischer, H.O.L., On the structure of galactinol (1953) J. Am. Chem. Soc., 75, pp. 4507-4509
  • Bean, R.C., Putman, E.W., Trucco, R.E., Hassid, W.Z., Preparation of C14-labeled D-galactose and glycerol (1953) J. Biol. Chem., 204, pp. 169-173
  • Gross, K.C., Changes in free galactose, myo-inositol and other monosaccharides in normal and non-ripening mutant tomatoes (1983) Phytochemistry, 22, pp. 1137-1139
  • Fukuda, M., Cell surface carbohydrates: Cell-type specific expression (1994) Molecular Glycobiology, pp. 1-52. , M. Fukuda and O. Hindsgaul (Eds.), Oxford University Press, Oxford
  • MacHer, B.A., Sweeley, C.C., Glycosphingolipids: Structure, biological source, and properties (1978) Methods Enzymol., 50, pp. 236-251
  • Lederkremer, R.M., Colli, W., Galactofuranose-containing glycoconjugates in trypanosomatids (1995) Glycobiology, 5, pp. 547-552
  • Wolfrom, M.L., Thompson, A., D-Galactose (1962) Methods Carbohydr. Chem., 1, pp. 120-122
  • Sturgeon, R.J., Enzymic determination of D-galactose (1994) Methods Carbohydr. Chem., 10, pp. 15-16
  • Bretting, H., Whittaker, N.F., Kabat, E.A., Königsmann-Lange, K., Thiem, H.-J., Chemical and inmunochemical studies on the structure of four snail galactans (1981) Carbohydr. Res., 98, pp. 213-236
  • Percival, E., Foyle, R.A.J., The extracellular polysaccharides of Porphyridium cruentum and Porphyridium aerugineum (1979) Carbohydr. Res., 72, pp. 165-176
  • Loentein, K., Lindberg, B., Lönngren, J., Assignment of absolute configuration of sugars by g.l.c. of their acetylated glycosides formed from chiral alcohols (1978) Carbohydr. Res., 62, pp. 359-362
  • Gerwig, G.J., Kamerling, J.P., Vliegenthart, J.F.G., Determination of the D and L configuration of neutral monosaccharides by high-resolution capillary g.l.c. (1978) Carbohydr. Res., 62, pp. 349-357
  • Sturgeon, R.J., Enzymic determination of L-galactose (1994) Methods Carbohydr. Chem., 10, pp. 17-19
  • Araki, C., Arai, K., L-Galactose (1962) Methods Carbohydr. Chem., 1, pp. 122-123
  • Dean, G.R., Acid hydrolysis of starch to D-glucose (1964) Methods Carbohydr. Chem., 4, pp. 249-250
  • MacAllister, R.V., Nutritive sweeteners made from starch (1979) Adv. Carbohydr. Chem. Biochem., 36, pp. 15-56
  • Yu, H.-M., Chen, S.-T., Suree, P., Nuansri, R., Wang, K.-T., Effect of microwave irradiation on acid-catalyzed hydrolysis of starch (1996) J. Org. Chem., 61, pp. 9608-9609
  • Kunlan, L., Lixin, X., Jun, L., Jun, P., Guoying, C., Zuwei, X., Salt-assisted acid hydrolysis of starch to D-glucose under microwave irradiation (2001) Carbohydr. Res., 331, pp. 9-12
  • Manners, D.J., Matheson, N.K., The fine structure of amylopectin (1981) Carbohydr. Res., 90, pp. 99-110
  • Norman, B.E., Enzymic conversion of starch into D-glucose syrup using glucoamylase and pullulanase (1994) Methods Carbohydr. Chem., 10, pp. 231-239
  • Wood, T.M., Enzymic conversion of cellulose into D-glucose (1994) Methods Carbohydr. Chem., 10, pp. 219-229
  • Behrend, R., Zur Kenntnis der β-Glucose (1910) Ann., 377, pp. 220-223
  • Mangam, A.W., Acree, S.F., The preparation of β-glucose (1917) J. Am. Chem. Soc., 39, pp. 965-968
  • Hudson, C.S., Dale, J.K., Studies on the forms of D-glucose and their mutarotation (1917) J. Am. Chem. Soc., 39, pp. 320-328
  • Whistler, R.L., Buchanan, B.F., Preparation of β-glucose (1938) J. Biol. Chem., 125, pp. 557-559
  • Lichtenthaler, F.W., Towards improving the utility of ketoses as organic raw materials (1998) Carbohydr. Res., 313, pp. 69-89
  • Ravenscroft, N., Walker, S.G., Dutton, G.G.S., Smit, J., Identification, isolation, and structural studies of extracellular polysaccharides produced by Caulobacter crescentus (1991) J. Bacteriol., 173, pp. 5677-5684
  • Becker, B., Hard, K., Melkonian, M., Kamerling, J.P., Vliegenthart, J.F.G., Identification of 3-deoxy-manno-2-octulosonic acid, 3-deoxy-5-O-methyl- manno-2-octulosonic acid and 3-deoxy-lyxo-2-heptulosaric acid in the cell wall (theca) of the green alga Tetraselmis striata Butcher (Prasinophyceae) (1989) Eur. J. Biochem., 182, pp. 153-160
  • Wagner, H., Habermeier, H., Schulten, H.-R., Die Herzglykoside des Pfeilgiftes von Lophopetalum toxicum Loher (1984) Helv. Chim. Acta, 67, pp. 54-63
  • Mengele, R., Sumper, M., Gulose as a constituent of a glycoprotein (1992) FEBS Lett., 298, pp. 14-16
  • Stuart, E.S., Tirrell, S.M., MacDonald, A.B., Characterization of an antigen secreted by Chlamydia-infected cell culture (1987) Immunology, 61, pp. 527-533
  • Fischer, E., Stahel, R., Zur Kenntniss der Xylose (1891) Ber., 24, pp. 528-539
  • Isbell, H.S., A new crystalline calcium chloride compound of α-D-glucose and its rotation and mutarotation in aqueous solution (1930) Bur. Standards J. Res., 5, pp. 741-755
  • Oshitari, T., Tomita, M., Kobayashi, S., New method for the preparation of L-gulose from L-mannose: Synthetic study on the sugar moiety of bleomycin (1994) Tetrahedron Lett., 35, pp. 6493-6494
  • Swain, M., Brisson, J.-R., Sprott, G.D., Cooper, F.P., Patel, G.B., Identification of β-L-gulose as the sugar moiety of the main polar lipid Thermoplasma acidophilum (1997) Biochim. Biophys. Acta, 1345, pp. 56-64
  • Uda, I., Sugai, A., Kon, K., Ando, S., Itoh, Y.H., Itoh, T., Isolation and characterization of novel neutral glycolipids from Thermoplasma acidophilum (1999) Biochim. Biophys. Acta, 1439, pp. 363-370
  • Whistler, R.L., Bemiller, J.N., L-Gulose (1962) Methods Carbohydr. Chem., 1, pp. 137-139
  • Isbell, H.S., Frush, H.L., α-D-Mannose (1962) Methods Carbohydr. Chem., 1, pp. 145-147
  • Fujita, T., Sato, T., A simple method for the preparation of crystalline D-mannose (1960) Bull. Chem. Soc. Jap., 33, p. 353
  • El Khadem, H., Sallam, M.A.E., The carbohydrate component of the doum-palm Kerner: Characterization and identification of a mannan (1967) Carbohydr. Res., 4, pp. 387-391
  • Amin, E.S., Paleologou, A.M., A study of the polysaccharides of the kernel and endocarp of the fruit of the Doum palm (Hyphaene thebaica) (1973) Carbohydr. Res., 27, pp. 447-450
  • Teixeira, A.Z.A., Iacomini, M., Gorin, P.A.J., An unusual glucomannan from Tornabenia intricata (1992) Phytochemistry, 31, pp. 3467-3470
  • Buckeridge, M.S., Panegassi, V.R., Rocha, D.V., Dietrich, S.M., Seed galactomannan in the classification and evolution of the Leguminosae (1994) Phytochemistry, 38, pp. 871-875
  • Kollár, R., Reinhold, B.B., Petráková, E., Yeh, H.J.C., Ashwell, G., Drgonová, J., Kapteyn, J.C., Cabib, E., Architecture of yeast cell wall (1997) J. Biol. Chem., 272, pp. 17762-17775
  • Gentzsch, M., Tanner, W., Protein-O-glycosylation in yeast: Protein-specific mannosyltransferases (1997) Glycobiology, 7, pp. 481-486
  • Kimura, Y., Takagi, S., Shiraishi, T., Occurrence of free N-glycans in pea (Pisum sativum. L) seedlings (1997) Biosci. Biotech. Biochem., 61, pp. 924-924
  • Sallam, M.A.E., Preparation of D-mannose from doum-palm kernels (1977) Carbohydr. Res., 53, pp. 134-135
  • Levine, S., Hansen, R.G., Sell, H.M., Preparation of β-D-mannopyranose and some derivatives (1968) Carbohydr. Res., 6, pp. 382-384
  • Kubelka, W., Kopp, B., Jentzsch, K., Ruis, H., Zur biogenese von strophanthidin-glykosiden: Convallatoxol als vorstufe von convallatoxin in Convallaria majalis (1974) Phytochemistry, 13, pp. 1080-1805
  • Jansson, P.-E., Kumar, N.S., Lindberg, B., Structural studies of a polysaccharide (S-88) elaborated by Pseudomonas ATCC 31544 (1986) Carbohydr. Res., 156, pp. 165-172
  • Jansson, P.-E., Lindberg, B., Widmalm, G., Structural studies of an extracellular polysaccharide (S-130) elaborated by Alcaligenes ATCC 31555 (1985) Carbohydr. Res., 139, pp. 217-223
  • Sowden, J.C., α-L-Glucose and α-L-mannose (1962) Methods Carbohydr. Chem., 1, pp. 132-135
  • Wiley, P.F., Sigal, M.V., Isolation of D-talose from a natural source (1958) J. Am. Chem. Soc., 80, pp. 1010-1011
  • Mann, R.L., Bromer, W.W., The isolation of a second antibiotic from Streptomyces hygroscopicus (1958) J. Am. Chem. Soc., 80, pp. 2714-2716
  • Neuss, N., Koch, K.F., Molloy, B.B., Day, W., Huckstep, L.L., Dorman, D.E., Roberts, J.D., Structure of Hygromycin B, an antibiotic from Streptomyces hygroscopicus: The use of CMR. Spectra in structure determination, I. (1970) Helv. Chim. Acta, 53, pp. 2314-2319
  • Fischer, E., Über ein neues Isomeres der galactonsaüre und der Schleimsaüre (1891) Ber., 24, pp. 3622-3629
  • Pigman, W.W., Isbell, H.S., β-D-Talose and D-talose acetates and orthoesters (1937) J. Res. Nat. Bur. Stand., 19, pp. 189-213
  • Horton, D., Jewell, J.S., Synthesis of 1,6-anhydro-β-D-talopyranose from derivatives of D-galactose and D-mannose (1967) Carbohydr. Res., 5, pp. 149-160
  • Chittenden, G.J.F., Oxidation of some derivatives of D-galactose with methyl sulphoxide-acid anhydride mixtures: A route to derivatives of D-glucose and D-talose (1970) Carbohydr. Res., 15, pp. 101-109
  • Barry, C.P., Honeyman, J., Fructose and its derivatives (1952) Adv. Carbohydr. Chem., 7, pp. 53-98
  • Verstraeten, L.M.J., D-Fructose and its derivatives (1967) Adv. Carbohydr. Chem., 22, pp. 229-305
  • Van Loo, J., Coussement, P., De Leenheer, L., Hoebregs, H., Smits, G., On the presence of inulin and oligofructose as natural ingredients in the western diet (1995) Crit. Rev. Food Sci. Nutr., 35, pp. 525-552
  • Flamm, G., Glinsmann, W., Kritchevsky, D., Prosky, L., Roberfroid, M., Inulin and oligofructose as dietary fiber: A review of the evidence (2001) Crit. Rev. Food Sci. Nutr., 41, pp. 353-362
  • Kawamura, M., Uchiyamana, T., Purification and some properties of cycloinulo-oligosaccharide fructanotransferase from Bacillus circulans OKUMZ 31B (1994) Carbohydr. Res., 260, pp. 297-304
  • Branefors-Helander, P., Structural studies of two capsular polysaccharides elaborated by strains of Haemophilus influenza type e (1981) Carbohydr. Res., 88, pp. 77-84
  • Bates, F.J., Levulose (1942) Polarimetry, Saccharimetry and the Sugars, Natl. Bur., pp. 398-401. , Standard Circular C440, United States Government Printing Office, Washington
  • Bhosale, S.H., Rao, M.B., Desphande, V.V., Molecular and industrial aspects of glucose isomerase (1996) Microbiol. Rev., 60, pp. 280-300. , and references cited there in
  • Häusler, H., Weber, H., Stütz, A.E., D-Xylose (D-glucose) isomerase (EC 5.3.1.5): Observations and comments concerning structural requirements of substrates as well as mechanistic features (2001) J. Carbohydr. Chem., 20, pp. 239-256
  • Hanover, L.M., White, J.S., Manufacturing, composition, and applications of fructose (1993) Am. J. Clin. Nutr., 58, pp. 724S-732S
  • Doddrell, D., Allerhand, A., Study of anomeric equilibria of ketoses in water by natural-abundance Carbon-13 Fourier Transform Nuclear Magnetic Resonance. D-Fructose and D-Turanose (1971) J. Am. Chem. Soc., 93, pp. 2779-2781
  • Angyal, S.J., The composition of reducing sugars in solution (1984) Adv. Carbohydr. Chem. Biochem., 42, pp. 15-68
  • Schroeder, W., Hoeksema, H., A new antibiotic, 6-amino-9-D-psicofuranosylpurine (1959) J. Am. Chem. Soc., 81, pp. 1767-1768
  • Garrett, E.R., Kinetics of the hydrolytic degradation of a nucleoside, the antibiotic psicofuranine (1960) J. Am. Chem. Soc., 82, pp. 827-832
  • Hough, L., Stacey, B.E., The occurrence of D-ribohexulose in Itea ilicifolia, Itea virginica, and Itea yunnanensis (1963) Phytochemistry, 2, pp. 315-320
  • Variation in the allitol content of Itea plants during photosynthesis (1966) Phytochemistry, 5, pp. 171-175
  • Biosynthesis and metabolism of allitol and D-allulose in Itea plants; incorporation of 14CO2 Phytochemistry, 5, pp. 215-222
  • Steiger, M., Reichstein, T., D-Psicose (1936) Helv. Chim. Acta, 19, pp. 184-188
  • Karabinos, J.V., Psicose, sorbose, and tagatose (1952) Adv. Carbohydr. Chem., 7, pp. 99-136
  • Martin, C.M., Reuter, F.H., Isolation of a pectic substance from passion fruit (Passiflora edulis) (1949) Nature, 164, pp. 407-407
  • Vitamin C (L-ascorbic acid) (1996) Ullmann's Encyclopedia of Industrial Chemistry, 5th Edn., A27, pp. 547-559. , Wiley-VCH
  • Hirst, E.L., Hough, L., Jones, J.K.N., Composition of the Gum of Sterculia setigera: Ocurrence of D-tagatose (1949) Nature, 163, p. 177
  • Bissett, D.L., Anderson, R.L., Isolation and properties of a class I D-ketohexose-1,6-diphosphate aldolase that catalyses the cleavage of D-tagatose-1,6-diphosphate (1980) J. Biol. Chem., 255, pp. 8750-8755
  • Kim, P., Yoon, S.H., Roh, H.J., Choi, J.H., High production of D-tagatose, a potential sugar substitute, using immobilized L-arabinose isomerase (2001) Biotechnol. Prog., 17, pp. 208-210
  • Roh, H.J., Kim, P., Park, Y.C., Choi, J.H., Bioconversion of D-galactose into D-tagatose by expression of L-arabinose isomerase (2000) Biotechnol. Appl. Biochem., 31, pp. 1-4
  • Totton, E.L., Lardy, H.A., The synthesis of D-tagatose by biochemical oxidation and by an improved chemical method (1949) J. Am. Chem. Soc., 71, p. 3076
  • Passeron, S., Recondo, E.E., Dicyclohexylcarbodi-imide: A new agent for carbohydrate epimerization and isomerization. Part I. Psicose formation (1965) J. Chem. Soc., pp. 813-815
  • Grünnagel, R., Haas, H.J., Darstellung von D-Tagatose (1969) Ann., 721, pp. 234-235
  • Reichstein, T., Weiss, E., The sugars of the cardiac glycosides (1962) Adv. Carbohydr. Chem., 17, pp. 65-120
  • Keller, M., Reichstein, T., Gofrusid, ein krystallisiertes glykosid aus den Samen von Gomphocarpus fruticosus (L.) R. Br.1 (1949) Helv. Chim. Acta, 32, pp. 1607-1612
  • Hunger, A., Reichstein, T., Die Konstitution von Gofrusid und Frugosid (1952) Helv. Chim. Acta, 35, pp. 1073-1103
  • Rees, R., Gavilanes, C.R., Meier, W., Früst, A., Meyer, K., Die Glykoside der Blätter von Digitalis canariensis L., var. isabelliana (WEBB) LINDIGER (1961) Helv. Chim. Acta, 44, pp. 1607-1622
  • Levene, P.A., Compton, J., The synthesis of D-allomethylose by a series of Walden inversions accompanying alkaline hydrolysis of 5-tosyl monoacetone L-Rhamnose (1936) J. Biol. Chem., 116, pp. 169-188
  • Gorshkova, R.P., Kalmykova, E.N., Isakov, V.V., Ovodov, Y.S., Structural studies of O-specific polysaccharides of lipopolysaccharides from Yersinia enterocolitica serovars O:1,2a,3, O:2a,2b,3 and O:3 (1985) Eur. J. Biochem., 150, pp. 527-531
  • Hoffman, J., Lindberg, B., Brubaker, R.R., Structural studies of O-specific side-chains of the polysaccharide from Yersinia enterocolitica Ye 128 (1980) Carbohydr. Res., 78, pp. 212-214
  • Korchagina, N.I., Gorshkova, R.P., Ovodov, Y.S., Studies on O-specific polysaccharide from Yersinia pseudotuberculosis VB serovar (1982) Bioorg. Khim., 8, pp. 1666-1669
  • Senchenkova, S.N., Shashkov, A.S., Moran, A.P., Helander, I.M., Knirel, Y.A., Structures of the O-specific polysaccharides chains of Pectinatus cerevisiiphilus and Pectinatus frisingensis lipopolysaccharides (1995) Eur. J. Biochem., 232, pp. 552-557
  • Uchio, Y., Nagasaki, M., Egushi, S., Matsuo, A., Nakayama, M., Hayashi, S., Labdane diterpene glycosides with 6-deoxy-L-idose from Aster spathulifolius maxim (1980) Tetrahedron Lett., 21, pp. 3775-3778
  • Hung, S.-C., Thopate, S.R., Puranik, R., Synthesis of 6-deoxy-L-idose and L-acovenose from 1,2:3,5-di-O- isopropylidene-α-D-glucofuranose (2001) Carbohydr. Res., 331, pp. 369-374
  • Kiliani, H., Über α-und β-Antiarin und über krystallisiertes eiweiß aus Antiaris-Saft (1913) Ber., 46, pp. 667-680
  • Moore, J.A., Tamm, C., Reichstein, T., Die Glykoside der Goldlacksamen, Cheiranthus cheiri L. (1954) Helv. Chim. Acta, 37, pp. 755-770
  • Zhang, L., Radziejewska-Lebrecht, J., Krajewska-Pietrasik, D., Toivanen, P., Skurnik, M., Molecular and chemical characterization of the lipopolysaccharide O-antigen and its role in the virulence of Yersinia enterocolitica serotype O:8 (1997) Mol. Microbiol., 23, pp. 63-76
  • Lerner, L.M., A simple preparation of 6-deoxy-D-gulose (1975) Carbohydr. Res., 44, pp. 116-1120
  • Zähringer, U., Rettenmaier, H., Moll, H., Senchenkova, S.N., Knirel, Y.A., Structure of a new 6-deoxy-α-D-talan from Burkholderia (Pseudomonas) plantarii strain DSM 6535, which is different from the O-chain of the lipopolysaccharide (1997) Carbohydr. Res., 300, pp. 143-151
  • Isshiki, Y., Matsuura, M., Dejsirilert, S., Ezaki, T., Kawahara, K., Separation of 6-deoxy-heptan from smooth type lipopolysaccharide preparation of Burkholderia pseudomallei (2001) FEMS Microbiol. Lett., 199, pp. 21-25. , Erratum in: ibid, 204 (2001) 391
  • Suzuki, N., Nakano, Y., Yoshida, Y., Nakao, H., Yamashita, Y., Koga, T., Genetic analysis of the gene cluster for the synthesis of serotype a-specific polysaccharide antigen Actinobacillus actinomycetemcomitans (2000) Biochim. Biophys. Acta, 1517, pp. 135-138
  • Shibuya, N., Amano, K., Azuma, J., Nishihara, T., Kitamura, Y., Noguchi, T., Koga, T., 6-Deoxy-D-talan and 6-deoxy-L-talan. Novel serotype-specific polysaccharide from Actinobacillus actinomycetemcomitans (1991) J. Biol. Chem., 266, pp. 16318-16323
  • Perry, M.B., MacLean, L.M., Brisson, J.R., Wilson, M.E., Structures of the antigenic O-polysaccharides of lipopolysaccharides produced by Actinobacillus actinomycetemcomitans serotypes a, c, d, and e (1996) Eur. J. Biochem., 242, pp. 682-688
  • Schmutz, J., Identifizierung der Zucker Komponente des Sarmentosid-A als L(-)-Talomethylose. Synthese der Krystallisierten L(-)-Talomethylose (1948) Helv. Chim. Acta, 31, pp. 1719-1723
  • Vanhaverbeke, C., Heyraud, A., Achouak, W., Heulin, T., Structural analysis of the exopolysaccharide from Burkholderia caribensis strain MWAP71 (2001) Carbohydr. Res., 334, pp. 127-133
  • Banaszek, A., Synthesis of the unique trisaccharide repeating unit, isolated from lipopolysaccharides Rhizobium leguminosarum bv. trifolii 24, and its analogue (1998) Carbohydr. Res., 306, pp. 379-385
  • Jachymek, W., Nieddziela, T., Petersson, C., Lugowowski, C., Czaja, J., Kenne, L., Structures of the O-specific polysaccharides from Yokenella regensburgei (Koserella trabulsii) strains PCM 2476,2477, 2478 and 2494: High-resolution magic-angle spinning NMR investigation of the O-specific polysaccharides in native lipopolysaccarides and directly on the surface of living bacteria (1999) Biochemistry, 38, pp. 11788-11795
  • Russa, R., Urbanik-Sypniewska, T., Linsdstrom, K., Mayer, H., Chemical characterization of two lipopolysaccharide species isolated from Rhizobium loti NZP2213 (1995) Arch. Microbiol., 163, pp. 345-351
  • Arbatsky, N.P., Shashkov, A.S., Toukach, F.V., Moll, H., Zych, K., Knirel, Y.A., Zähringer, U., Sidorczyk, Z., Structure of the O-specific polysaccharide of serologically separate strain Proteus penneri 2 from a new proposed serogroup 066 (1999) Eur. J. Biochem., 261, pp. 392-397
  • Jann, B., Shashkov, A., Torgov, V., Kochanowski, H., Seltmann, G., Jann, K., NMR investigation of the 6-deoxy-L-talose-containing O45, O45-related (O45rel), and O66 polysaccharides of Escherichia coli (1995) Carbohydr. Res., 278, pp. 155-165
  • Knirel, Y.A., Zdorovenko, G.M., Veremeichenko, S.N., Shashkov, A.S., Zakharova, I.I., Kochetkov, N.K., Antigenic bacterial polysaccharides. 36. A study of the structure of the O-specific polysaccharide chain of the lipopolysaccharide of Pseudomonas fluorescens IMV 2763 (biostrain G) (1989) Bioorg. Khim., 15, pp. 1538-1545
  • Wilkinson, S.G., Galbraith, L., Anderton, W.J., Lipopolysaccharides from Pseudomonas maltophilia: Composition of the lipopolysaccharide and structure of the side-chain polysaccharide from strain N.C.I.B. 9204 (1983) Carbohydr. Res., 112, pp. 241-252
  • Aspinall, G.O., Gammon, D.W., Sood, R.K., Chatterjee, D., Rivoire, B., Brennan, P.J., Structures of the glycopeptidolipid antigens of serovars 25 and 26 of the Mycobacterium avium serocomplex, synthesis of allyl glycosides of the outer disaccharide units and serology of the derived neoglycoproteins (1992) Carbohydr. Res., 237, pp. 57-77
  • Collins, P.M., Overend, W.G., A synthesis of 6-deoxy-L-talose (1965) J. Chem. Soc., pp. 1912-1918
  • Defaye, J., Gadelle, A., Angyal, S.A., An efficient synthesis of L-fucose and L-(4-2H)fucose (1984) Carbohydr. Res., 126, pp. 165-169
  • Aspinall, G.O., Takeo, K., Derivatives of 6-deoxy-L-talose and the synthesis of 6-deoxy-2-O- (α-L-rhamnopyranosyl)-L-talose (1983) Carbohydr. Res., 126, pp. 165-169
  • Votoek, E., Valentin, F., Rhamnoconvolvulic acid (1929) Collect. Czech. Chem. Comm., 1, pp. 47-54
  • Power, F.B., Rogerson, H., Chemical examination of the root of Ipomoea orizabensis (1912) J. Chem. Soc., 101, pp. 1-26
  • Davies, L.A., Adams, R., Structures of convolvulinolic and jalapinolic acids. Synthesis of 11-hydroxypentadecanoic and 11-hydroxyhexadecanoic acids (1928) J. Am. Chem. Soc., 50, pp. 1749-1755
  • Mannich, C., Schumann, P., Jalap resin and its principal constituents, convolvulin (1938) Arch. Pharm., 276, pp. 211-226
  • Bruno, I., Minale, L., Riccio, R., Starfish saponins, part 43. Structures of two new sulfated steroidal fucofuranosides (imbricatosides a and B) and six new polyhydroxysteroids from starfish Dermasterias imbricata (1990) J. Nat. Prod., 53, pp. 366-374
  • Amano, K., Nishihara, T., Shibuya, N., Noguchi, T., Koga, T., Immunochemical and structural characterization of a serotype-specific polysaccharide antigen from Actinobacillus actinomycetemcomitans Y4 (serotype b) (1989) Infect. Immun., 57, pp. 2942-2946
  • Ravenscroft, N., Walker, S.G., Dutton, G.G.S., Smit, J., Identification, isolation, and structural studies of extracellular polysaccharides produced by Caulobacter crescentus (1991) J. Bacteriol., 173, pp. 5677-5684
  • Sato, N., Nakazawa, Sato, M., Hoshino, I., Ito, T., Structural studies of the antigenic polysaccharide of Eubacterium saburreum, strain T19 (1993) Carbohydr. Res., 245, pp. 105-111
  • Hoffman, J., Lindberg, B., Hofstad, T., Lygre, H., Structural studies of the polysaccharide antigen of Eubacterium saburreum, strain L452 (1977) Carbohydr. Res., 58, pp. 439-442
  • Winn, A.M., Miles, C.T., Wilkinson, S.G., Structure of the O3 antigen of Stenotrophomonas (Xanthomonas or Pseudomonas) maltophilia (1996) Carbohydr. Res., 282, pp. 149-156
  • Winn, A.M., Galbraith, L., Temple, G.S., Wilkinson, S.G., Structure of the O19 antigen of Xanthomonas maltophilia (1993) Carbohydr. Res., 247, pp. 249-254
  • Knirel, Y.A., Shashkov, A.S., Soldatkina, M.A., Paramonov, N.A., Zakharova, I.I., Antigenic polysaccharides of bacteria. 32. The structure of O-specific polysaccharide chains of Pseudomonas cepacia serotype B and e lipopolysaccharides containing D-fucose (1988) Bioorg. Khim., 14, pp. 1208-1213
  • Gaur, D., Galbraith, L., Wilkinson, S.G., Structural characterization of a rhamnan and a fucorhamnan, both present in the lipopolysaccharide of Burkholderia vietnamiensis strain LMG 10926 (1998) Eur. J. Biochem., 258, pp. 696-701
  • Ray, T.C., Smith, A.R., Wait, R., Hignett, R.C., Structure of the sidechain of lipopolysaccharide from Erwinia amylovora T. (1987) Eur. J. Biochem., 170, pp. 357-361
  • Flowers, H.M., The chemistry and biochemistry of D- and L-fucose (1981) Adv. Carbohydr. Chem. Biochem., 39, pp. 279-345
  • Chevolot, L., Foucault, A., Chaubet, F., Kervarec, N., Sinquin, C., Fisher, A.-M., Boisson-Vidal, C., Further data on the structure of brown seaweed fucans: Relationships with anticoagulant activity (1999) Carbohydr. Res., 319, pp. 154-165
  • Kariya, Y., Watabe, S., Kyogashima, M., Ishihara, M., Ishii, T., Structure of fucose branches in the glycosaminoglycan from the body wall of the sea cucumber Stichopus japonicus (1997) Carbohydr. Res., 297, pp. 273-279
  • Stults, C.L.M., Sweeley, C.C., MacHer, B.A., Glycosphingolipids: Structure, biological source and properties (1989) Methods in Enzymol., 179, pp. 167-214
  • Lowe, J.B., Ligands for E-selectin-biosynthesis of sialylated, fucosylated oligosaccharides (1994) Molecular Glycobiology, pp. 177-178. , M. Fukuda and O. Hindsgaul (Eds.), Oxford University Press, Oxford
  • Moloney, D.J., Lin, A.I., Haltiwagner, R.S., The O-linked fucose glycosylation pathway (1997) J. Biol. Chem., 272, pp. 19046-19050
  • Newburg, D.S., Pickering, L.K., McCluer, R.H., Cleary, T.G., Fucosylated oligosaccharides of human milk protect suckling mice from heat-stabile enterotoxin of Escherichia coli (1990) J. Infect. Dis., 162, pp. 1075-1080
  • Rasko, D.A., Wang, G., Palcic, M.M., Taylor, D.E., Cloning and characterization of the α(1,3/4) fucosyltransferase of Helicobacter pylori (2000) J. Biol. Chem., 275, pp. 4988-4994
  • Hockett, R.C., Phelps, F.P., Hudson, C.S., Relations between rotatory power and structure in the sugar group. XXXIII. The alpha and beta methyl pyranosides of L-fucose (L-galactomethylose) and their triacetates (1939) J. Am. Chem. Soc., 61, pp. 1658-1660
  • Freudenberg, K., Raschig, K., Acetonesugars. XVI. L-Altromethylose, quinovose ando digitoxe. The system of the methylpentoses (1929) Ber., 62, pp. 373-383
  • Haridas, V., Higuchi, M., Jayatilake, G.S., Bailey, D., Mujoo, K., Blake, M.E., Gutterman, J.U., Avicins: Triterpenoid saponins from Acacia victoriae (bentham) induce apoptosis by mitochondrial perturbation (2001) Proc. Natl. Acad. Sci., 98, pp. 5821-5826
  • Fang, Y., Chai, W., Chen, S., He, Y., Zhao, L., Peng, J., Huang, H., Xin, B., On the structure of calonyctin A, a plant growth regulator (1993) Carbohydr. Res., 245, pp. 259-270
  • Hebermehl, G.G., Krebs, H.C., Toxins of Echinoderms (1990) Studies in Natural Products Chemistry, 7, pp. 265-316. , Atta-ur-Rahman (Ed.), Elsevier Science
  • Schmidt, O.T., 6-Deoxy-α-D-glucose (D-Quinovose) (1962) Methods Carbohydr. Chem., 1, pp. 198-201
  • Pathirana, C., Jensen, P.R., Dwight, R., Fenical, W., Rare phenazine L-quinovose esters from marine actinomycete (1992) J. Org. Chem., 57, pp. 740-742
  • Sonesson, A., Jantzen, E., Tangen, T., Zähringer, U., Chemical characterization of lipopolysaccharides from Legionella feeleii, Legionella hackeliae and Legionella jordanis (1994) Microbiology, 140, pp. 2663-2671
  • Kocharova, N.A., Knirel, Y.A., Widmalm, G., Jansson, P.-E., Moran, A.P., Structure of an atypical O-antigen polysaccharide of Helicobacter pylori containing a novel monosaccharide 3-C-methyl-D-mannose (2000) Biochemistry, 39, pp. 4755-4760
  • Winn, A.M., Wilkinson, S.G., The O7 antigen of Stenotrophomonas maltophilia is a linear D-rhamnan with a trisaccharide repeating unit that is also present in polymers for some Pseudomonas and Burkholderia species (1998) FEMS Microbiol. Lett., 166, pp. 57-61
  • Senchenkova, S.N., Shashkov, A.S., Knirel, Y.A., McGovern, J.J., Moran, A.P., The O-specific polysaccharide chain of Campylobacter fetus serotype e lipopolysaccharide is a D-rhamnan terminated with 3-O-methyl-D-rhamnose (D-acofriose) (1996) Eur. J. Biochem., 239, pp. 434-438
  • Kocharova, N.A., Borisova, S.A., Zatonsky, G.V., Shashkov, A.S., Knirel, Y.A., Kholodkova, E.V., Staniskavsky, E.S., Structure of the O-specific polysaccharide of Citrobacter freundii O3a,3b,1c (1998) Carbohydr. Res., 306, pp. 331-333
  • Zorbach, W.W., Tio, C.O., A new synthesis of D-rhamnose (6-deoxy-D-mannose) (1961) J. Org. Chem., 26, pp. 3543-3545
  • Zhan, D., Janssen, P., Mort, A.J., Scarcity or complete lack of single rhamnose residues interspersed within the homogalacturan regions of citrus pectin (1998) Carbohydr. Res., 308, pp. 373-380
  • Escribano, J., Rios, I., Fernández, J.A., Isolation and cytotoxic properties of a novel glycoconjugate from the corm of saffron plant (Crocus sativus L.) (1999) Biochim. Biophys. Acta, 1426, pp. 217-222
  • An, J., Carlson, R.W., Glushka, J., Streeter, J.G., The structure of a novel polysaccharide produced by Bradyrhizobium species within soybean nodules (1995) Carbohydr. Res., 269, pp. 303-317
  • Gonda, R., Tomoda, M., Shimizu, N., Yamada, H., Structure and anticomplementary activity of an acidic polysaccharide from the leaves of Malva sylvestris var. mauritiana (1990) Carbohydr. Res., 198, pp. 323-329
  • Lee, J.-B., Hayashi, T., Hayashi, K., Sankawa, U., Structural analysis of calcium spirulan (Ca-SP)-derived oligosaccharides using electrospray ionization mass spectrometry (2000) J. Nat. Prod., 63, pp. 136-138
  • Guo, S., Kenne, L., Characterization of some O-acetylated saponins from Quillaja saponaria Molina (2000) Phytochemistry, 54, pp. 613-615
  • Flezanka, T., Gushina, I.A., Glycosidic compounds of murolic, protoconstipatic and allo-murolic acids from lichens of Central Asia (2000) Phytochemistry, 54, pp. 635-645
  • Jansson, P.-E., Lindberg, B., Anderson, M., Lindquist, U., Henrichsen, J., Structural studies of the capsular polysaccharide from Streptococcus pneumoniae type 2, a reinvestigation (1988) Carbohydr. Res., 182, pp. 111-117
  • Marshall, V.M., Dunn, H., Elvin, M., McLay, N., Gu, Y., Laws, A.P., Structural characterization of the exopolysaccharide produced by Streptococcus thermophilus EU20 (2001) Carbohydr. Res., 331, pp. 413-422
  • Faber, E.J., Van Der Haak, M.J., Kamerling, J.P., Vliegenthart, J.F., Structure of the exopolysaccharide produced by Streptococcus thermophilus S3 (2001) Carbohydr. Res., 331, pp. 173-182
  • MacLean, L.L., Vinogradov, E., Crump, E.M., Perry, M.B., Kay, W.W., The structure of the lipopolysaccharide O-antigen produced by Flavobacterium psychrophilum (259-293) (2001) Eur. J. Biochem., 268, pp. 2710-2716
  • Paramonov, N., Bailey, D., Rangarajan, M., Hashim, A., Kelly, G., Curtis, M.A., Hounsell, E.F., Structural analysis of the polysaccharide from the lipopolysacchatide of Porphyromonas gingivalis strain W50 (2001) Eur. J. Biochem., 268, pp. 4698-4707
  • Perry, M.B., MacLean, L.L., Structural identification of the lipopolysaccharide O-antigen produced by Yersinia enterocolitica serotype O:28 Eur. J. Biochem., 267, pp. 2567-2572
  • Shashkov, A.S., Senchenkova, S.N., Laux, P., Ahohuendo, B.C., Kecskes, M.L., Rudolph, K., Knirel, Y.A., Structure of the O-chain polysaccharide of the lipopolysaccharide of Xanthomonas campestris pv. manihotis GSPB 2755 and GSPB 2364 (2000) Carbohydr. Res., 323, pp. 235-239
  • McNeil, M.R., Gaylord, H., Brennan, P.J., N-Formylkansosaminyl-(1→3)-2-O-methyl-D-rhamnopyranose: The type-specific determinant of serovariant 14 of the Mycobacterium avium complex (1988) Carbohydr. Res., 177, pp. 185-198
  • Aspinall, G.O., Chatterjee, D., Brennan, P.J., The variable surface glycolipids of Mycobacteria: Structures, synthesis of epitopes, and biological properties (1995) Adv. Carbohydr. Chem. Biochem., 51, pp. 169-242
  • Christian, R., Schulz, G., Unger, F.M., Messner, P., Kupcu, Z., Sleytr, U.B., Structure of a rhamnan from the surface-layer glycoprotein of Bacillus stearothermophilus strain NRS 2004/3a (1986) Carbohydr. Res., 150, pp. 265-272
  • Messner, P., Sleytr, U.B., Asparaginyl-rhamnose: A novel type of protein-carbohydrate linkage in a eubacterial surface-layer glycoprotein (1988) FEBS Lett., 228, pp. 317-320
  • Haynes, P.A., Ferguson, M.A.J., Cross, G.A.M., Structural characterization of novel oligosaccharides of cell-surface glycoproteins of Trypanosoma cruzi (1996) Glycobiology, 6, pp. 869-878
  • Wolfrom, M.L., Thompson, A., 6-Deoxy-α-L-mannose (α-L-Rhamnose) monohydrate (1962) Methods Carbohydr. Chem., 1, pp. 202-204
  • Richtmyer, N.K., The isolation of volemitol and other polyhydric alcohols from avocado seeds (1970) Carbohydr. Res., 12, pp. 135-138
  • Holst, O., Brade, H., Chemical structure of the core region of lipopolysaccharides (1992) Bacterial Endotoxic Lipopolysaccharides, pp. 135-170. , D. C. Morrison and J. L. Ryan (Eds.), CRC Press, Boca Raton, Florida
  • Zdorovenko, G.M., Shashkov, A.S., Zdorovenko, E.L., Kocharova, N.A., Yakovleva, L.M., Knirel, Y.A., Rudolph, K., Characterization of the lipopolysaccharide and structure of the O-specific polysaccharide of the bacterium Pseudomonas syringae pv. atrofaciens IMV 948 (2001) Biochemistry (Mosc), 66, pp. 369-377
  • Mansson, M., Bauer, S.H., Hood, D.W., Richards, J.C., Moxon, E.R., Schweda, E.K., A new structural type for Haemophilus influenzae lipopolysaccharide. Structural analysis of the polysaccharide from nontypeable Haemophilus influenzae strian 486 (2001) Eur. J. Biochem., 268, pp. 2148-2159
  • Moran, A.P., Helanderand, I.M., Kosumen, T.U., Compositional analysis of Helicobacter pylori rough-form lipopolysaccharides (1992) J. Bacteriol., 174, pp. 1370-1377
  • Aspinall, G.O., Monteiro, M.A., Pang, H., Walsh, E.J., Moran, A.P., Lipopolysaccharide of the Helicobacter pylori type strain NCTC 11637 (ATCC 43504): Structure of the O antigen chain and core oligosaccharide regions (1996) Biochemistry, 35, pp. 2489-2497
  • Senchenkova, S.N., Zatonsky, G.V., Hynes, S.O., Widmalm, G., Andersen, L.P., Knirel, Y.A., Jansson, P.-E., Moran, A.P., Structure of a D-glycero-D-manno-heptan from the lipopolysaccharide of Helicobacter pylori (2001) Carbohydr. Res., 331, pp. 219-224
  • Oertelt, C., Lindner, B., Skurnik, M., Holst, O., Isolation and structural characterization of an R-form lipopolysaccharide from Yersinia enterocolitica serotype O:8 (2001) Eur. J. Biochem., 268, pp. 554-564
  • Brimacombe, J.S., Kabir, A.K.M.S., Convenient synthesis of L-glycero-D-manno-heptose and D-glycero-D-manno-heptose (1986) Carbohydr. Res., 152, pp. 329-334. , and reference cited therein
  • Sen, A.K., Mukherjee, A.K., Guhathakurta, B., Dutta, A., Sasmal, D., Studies on the partial structure of the O-antigen of Vibrio cholera, Inaba 569 B (1980) Carbohydr. Res., 86, pp. 113-121
  • Aspinall, G.O., McDonald, A.G., Pang, H., Structures of the O chains from the lipopolysaccharides of Campylobacter jejuni serotypes O:23 and O:36 (1992) Carbohydr. Res., 231, pp. 13-30
  • Sephton, H.H., Richtmyer, N.K., The isolation of a second octulose and of a heptose from the Avocado: D-glycero-L-galacto-octulose and D-glycero-D-galacto-heptose (1963) J. Org. Chem., 28, pp. 1691-1694
  • MacLennan, A.P., Davies, D.A.L., The isolation of D-glycero-D-galacto-heptose and other sugar components from the specific polysaccharide of Chromobacterium violaceum (BN) (1957) Biochem. J., 66, pp. 562-567
  • Vinogradov, E.V., Brade, H., Holst, O., The stucture of the O-specific polysaccharide of the lipopolysaccharide from Chromobacterium violaceum NCTC 9694 (1994) Carbohydr. Res., 264, pp. 313-317
  • Hoffman, J., Lindberg, B., Svensson, S., Hofstad, T., Structure of the polysaccharide antigen of Eubacterium saburreum, strain L44 (1974) Carbohydr. Res., 35, pp. 49-53
  • Hoffman, J., Lindberg, B., Lönngren, J., Hofstad, T., Structural studies of the polysaccharide antigen of Eubacterium saburreum, strain 49 (1976) Carbohydr. Res., 47, pp. 261-267
  • Kondo, W., Sato, N., Ito, T., Chemical structure of the polysaccharide antigen of Eubacterium saburreum, strain O2 (1979) Carbohydr. Res., 70, pp. 117-123
  • Hoffman, J., Lindberg, B., Skaug, N., Hofstad, T., Structural studies of the Eubacterium saburreum strain O2 antigen (1980) Carbohydr. Res., 84, pp. 181-183
  • Kondo, W., Nakasawa, T., Ito, T., Structural studies of the antigenic polysaccharide of Eubacterium saburreum, strain S29 (1981) Carbohydr. Res., 97, pp. 279-283
  • Kondo, W., Nakasawa, F., Sato, M., Ito, T., Structural studies of the antigenic polysaccharide of Eubacterium saburreum, strain T27 (1983) Carbohydr. Res., 117, pp. 125-131
  • Nakasawa, F., Structural studies of the antigenic polysaccharide of Eubacterium saburreum, strain T17 (1985) Carbohydr. Res., 143, pp. 185-190
  • Nakasawa, F., Hoshino, E., Immunochemical and structural characterization of the antigenic polysaccharide from Eubacterium saburreum T18 (1992) Oral Microbiol. Immunol., 7, pp. 182-186
  • Begbie, R., Richtmyer, N.K., The isolation of some heptoses, heptuloses, octuloses, and nonuloses from Primula officinalis Jacq. (1966) Carbohydr. Res., 2, pp. 272-288
  • Majumder, M., Mukherjee, A.K., Thakurta, B.G., Dutta, A., Sasmal, D., Studies on the partial structure of the O-antigen of Vibrio cholera Ogawa G-2102 (1983) Carbohydr. Res., 122, pp. 209-216
  • Aspinall, G.O., Monteiro, M.A., Pang, H., Kurjanczyk, L.A., Penner, J.L., Lipo-oligosaccharide of Campylobacter lari strain PC 637. Structure of the liberated oligosaccharide and an associated extracellular polysaccharide (1995) Carbohydr. Res., 279, pp. 227-244
  • Aspinall, G.O., Monteiro, M.A., Pang, H., Lipo-oligosaccharide of Campylobacter lari type strain ATCC 35211. Structure of the liberated oligosaccharide and an associated extracellular polysaccharide (1995) Carbohydr. Res., 279, pp. 245-264
  • Hellerqvist, C.G., Lindberg, B., Samuelsson, K., Brubaker, R.R., Structural studies of the O-specific side-chains of the cell-wall lipopolysaccharide from Pasteurella pseudotuberculosis Group IIA (1972) Acta. Chem. Scand., 26, pp. 1389-1393
  • Knirel, Y.A., Paramonov, N.A., Shashkov, A.S., Kochetkov, N.K., Yarullin, R.G., Farber, S.M., Efremenko, V.I., Structure of the polysaccharide chains of Pseudomonas pseudomallei lipopolysaccharides (1992) Carbohydr. Res., 233, pp. 185-193
  • Aspinall, G.O., McDonald, A.G., Pang, H., Kurjanczyk, L.A., Penner, J.L., An antigenic polysaccharide from of Campylobacter coli serotype O:30. Structure of a teichoic acid-like antigenic polysaccharide associated with the lipopolysaccharide (1993) J. Biol. Chem., 268, pp. 18321-18329
  • Pratt, J.W., Richtmyer, N.K., D-glycero-D-allo-Heptose, L-allo-heptose , D-talo-heptulose and related substances derived from the addition of cyanide to D-allose (1955) J. Am. Chem. Soc., 77, pp. 6326-6328
  • Schaffer, R., Synthesis of higher ketoses by aldol reactions. II. Unnsubstituted heptuloses (1964) J. Org. Chem., 29, pp. 1471-1473
  • Schaffer, R., The isomerization of D-manno-3-heptulose by alkali (1964) J. Org. Chem., 29, pp. 1473-1475
  • Johansson, I., Richtmyer, N.K., The isolation of both talo-heptulose and an allo-heptulose from the avocado. Some new paper-chromatographic data on heptuloses (1970) Carbohydr. Res., 13, pp. 461-464
  • Gray, A., Okuda, T., Konishi, K., Isolation and structure of coriose, a natural 3-heptulose (1968) Chem. Commun., pp. 553-554
  • Okuda, T., Konishi, K., The formation of several products from the trimethylsilylation of D-altro-3-heptulose ("coriose") (1969) Chem. Commun., pp. 1117-1118
  • Okuda, T., Konishi, K., Coriose and related compounds. I. Isolation of coriose and co-occuring carbohydrates from leaf, stem, and fruit of Coriaria japonic (1968) Yakugaku Zacchi, 88, pp. 1329-1332
  • Okuda, T., Konishi, K., Structure and some reactions of coriose (1968) Tetrahedron, 24, pp. 6907-6912
  • Okuda, T., Osaki, K., Taga, T., α-Coriofuranose: Conformationally unfavoured structure in the crystalline state and rapid mutarotation of coriose (1969) Chem. Commun., pp. 851-852
  • Laforge, F.B., D-Mannoketoheptose, a new sugar from the avocado (1917) J. Biol. Chem., 28, pp. 511-522
  • Richtmyer, N.K., D-manno-Heptulose (1962) Methods Carbohydr. Chem., 1, pp. 173-175
  • Haustveit, G., Wold, J.K., Some carbohydrates of low molecular weight present in Cannabis sativa L. (1973) Carbohydr. Res., 29, pp. 325-329
  • Stankovic, L., Bilik, V., Occurrence and preparation of D-manno-heptulose (1986) Chem. Listy, 80, pp. 520-527
  • Montgomery, E.M., Hudson, C.S., The synthesis of D-mannoheptulose, and the preparation of some of its derivatives (1939) J. Am. Chem. Soc., 61, pp. 1654-1658
  • Okuda, T., Mori, K., Distribution of manno-heptulose and sedoheptulose in plants (1974) Phytochemistry, 13, pp. 961-964
  • Percival, E., Young, M., Carbohydrates of the seaweeds. Part III. Desmarestia aculeata (1974) Carbohydr. Res., 32, pp. 195-201
  • Häfliger, B., Kindhauser, E., Keller, F., Metabolism of D-glycero-D-manno-heptitol, volemitol, in Polyanhus. Discovery of a novel ketose reductase (1999) Plant Physiology, 119, pp. 191-197
  • Kremer, B.P., Biosynthesis of polyols in Pelvetia canaliculata (1977) Z. Pflanzenphysiol., 81, pp. 68-73
  • Richtmyer, N.K., Hann, R.M., Hudson, C.S., The oxidative degradation of sedoheptulose to D-altronic acid (1939) J. Am. Chem. Soc., 61, pp. 343-345
  • Pratt, J.W., Richtmyer, N.K., Hudson, C.S., The structure of sedoheptulosan (1951) J. Am. Chem. Soc., 73, pp. 1876-1877
  • Proof of the structure of sedoheptulosan as 2,7-anhydro-β-D- altroheptulopyranose (1952) J. Am. Chem. Soc., 74, pp. 2200-2205
  • Richtmyer, N.K., Pratt, J.W., Sedoheptulose. Its rotation, reducing power, equilibrium with sedoheptulosan in acid solution, and crystalline hexaacetate; Also crystalline 2,7-anhydro-β-D-altro-heptulofuranose (1956) J. Am. Chem. Soc., 78, pp. 4717-4721
  • Demuynck, C., Bolte, J., Hecquet, L., Dalmas, V., Enzyme-catalyzed synthesis of carbohydrates: Synthetic potential of transketolase (1991) Tetrahedron Lett., 32, pp. 5085-5088
  • Charlson, A.J., Richtmyer, N.K., The isolation of an octulose and an octitol from natural sources: D-glycero-D-manno-octulose and D-erythro-D-galacto-octitol from the Avocado and D-glycero-D-manno-octulose from Sedum species (1960) J. Am. Chem. Soc., 82, pp. 3428-3434
  • Sephton, H.H., Richtmyer, N.K., The isolation of D-erythro-L-galacto-nonulose from the Avocado, together with its synthesis and proof of structure through reduction to D-arabino-D-manno-nonitol and D-arabino-D-gluco-nonitol (1966) Carbohydr. Res., 2, pp. 289-301
  • Haustveit, G., McComb, E.A., Rendig, V.V., Biosynthesis of D- and L-glycero-L-galacto-octulose from pentoses and hexoses (1975) Carbohydr. Res., 39, pp. 125-129
  • Haustveit, G., McComb, E.A., Rendig, V.V., Biosynthesis of D-glycero-D-altro-octulose from D-ribose and D-allose (1975) Carbohydr. Res., 41, pp. 363-365
  • Haustveit, G., Aldolase-catalysed formation of D-glycero-D-manno-octulose from D-ribose and D-fructose 1,6-diphosphate (1976) Carbohydr. Res., 47, pp. 164-166
  • Bianchi, G., Gamba, A., Murelli, C., Salamini, F., Bartels, D., Novel carbohydrate metabolism in the resurrection plant Craterostigma plantagineum (1991) The Plant Journal, 1, pp. 335-339
  • Howarth, O.W., Pozzi, N., Vlahov, G., Bartels, D., NMR structural analysis of a tri-O-isopropylidene derivative of D-glycero-D-ido-2-octulose, the major sugar found in the resurrection plant Craterostigma plantagineum (1996) Carbohydr. Res., 289, pp. 137-142
  • Schwall, G., Elster, R., Ingram, J., Bernacchia, G., Gallagher, L., Salamini, F., Bartels, D., Carbohydrate metabolism in the desiccation tolerant plant Craterostigma plantagineum Hochst (1995) Sucrose Metabolism, Biochemistry, Physiology, and Molecular Biology, Current Topics in Plant Physiology, 14, pp. 245-253. , H. Pontis, G. Salerno, and E. Echeverria (Eds.), American Society of Plant Physiologists
  • Norwood, M., Truesdale, M.R., Richter, A., Scott, P., Photosynthetic carbohydrate metabolism in the resurrection plant Craterostigma plantagineum (1995) J. Exp. Botany, 51, pp. 159-165
  • Sakata, K., Hagiwara, H., Yagi, A., Ina, K., The first naturally occurring 3-octulose, D-gluco-L-glycero-3-octulose, as the main constituent of Laurus nobilis Flush (1989) Agric. Biol. Chem., 53, pp. 2539-2541
  • Sephton, H.H., Richtmyer, N.K., Isolation of D-erythro-L-gluco-nonulose from the Avocado (1963) J. Org. Chem., 28, pp. 2388-2390
  • Wolfrom, M.L., Wood Jr., H.B., Two 3-epimeric ketononoses (1954) J. Am. Chem. Soc., 77, pp. 3096-3098
  • Bednarski, M.D., Waldmann, H.J., Whitesides, G.M., Aldolase-catalyzed synthesis of complex C8 and C9 monosaccharides (1986) Tetrahedron Lett., 27, pp. 5807-5810

Citas:

---------- APA ----------
De Leder Kremer, R.M. & Gallo-Rodriguez, C. (2004) . Naturally occurring monosaccharides: Properties and synthesis. Advances in Carbohydrate Chemistry and Biochemistry, 59, 9-67.
http://dx.doi.org/10.1016/S0065-2318(04)59002-9
---------- CHICAGO ----------
De Leder Kremer, R.M., Gallo-Rodriguez, C. "Naturally occurring monosaccharides: Properties and synthesis" . Advances in Carbohydrate Chemistry and Biochemistry 59 (2004) : 9-67.
http://dx.doi.org/10.1016/S0065-2318(04)59002-9
---------- MLA ----------
De Leder Kremer, R.M., Gallo-Rodriguez, C. "Naturally occurring monosaccharides: Properties and synthesis" . Advances in Carbohydrate Chemistry and Biochemistry, vol. 59, 2004, pp. 9-67.
http://dx.doi.org/10.1016/S0065-2318(04)59002-9
---------- VANCOUVER ----------
De Leder Kremer, R.M., Gallo-Rodriguez, C. Naturally occurring monosaccharides: Properties and synthesis. Adv. Carbohydr. Chem. Biochem. 2004;59:9-67.
http://dx.doi.org/10.1016/S0065-2318(04)59002-9