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Abstract:

2-Amino-2,3-dideoxy-d-manno-heptonic acid (7) has been synthesized from 2,5,6,7-tetra-O-acetyl-3-deoxy-d-gluco-heptono-1,4-lactone (1), which was readily prepared from d-glycero-d-gulo-heptono-1,4-lactone. O-Deacetylation of 1 followed by treatment with 13:1 (v/v) 2,2-dimethoxypropane/acetone in the presence of p-toluenesulfonic acid gave methyl 3-deoxy-4,5:6,7-di-O-isopropylidene-d-gluco-heptonate (3) as a crystalline product (80% yield). The free hydroxyl group (OH-2) of 3 was mesylated and substituted by azide to give the corresponding azide derivative 5. Hydrogenolysis and further hydrolysis of the ester function of 5 afforded α-amino acid 7 (43% overall yield from 1). Compound 7 is an analog of l-alanine having a polyhydroxy chain attached to C-3. The diastereoisomer of 7 at C-2, 2-amino-2,3-dideoxy-d-gluco-heptonic acid (12) was also prepared from 3, by a route that involved 2,3-dideoxy-2-iodo derivative 8 as a key intermediate. © 2006 Elsevier Ltd. All rights reserved.

Registro:

Documento: Artículo
Título:Synthesis of polyhydroxy amino acids based on d- and l-alanine from d-glycero-d-gulo-heptono-1,4-lactone
Autor:Gómez, R.V.; Kolender, A.A.; Varela, O.
Filiación:CIHIDECAR-CONICET, Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Pabellon II, Ciudad Universitaria, 1428 Buenos Aires, Argentina
Palabras clave:Acetonation; d-Alanine; l-Alanine; Polyhydroxy amino acids; Sugar amino acids; Acetone; Hydrolysis; Organic polymers; Substitution reactions; Synthesis (chemical); Acetonation; d-Alanine; l-Alanine; Polyhydroxy amino acids; Sugar amino acids; Amino acids; acetone; alanine; alpha amino acid; amino acid derivative; azide; dextro alanine; ester; hydroxyl group; lactone derivative; propane; sulfonic acid derivative; amino acid synthesis; article; deacetylation; diastereoisomer; hydrogenolysis; hydrolysis; priority journal; substitution reaction; Alanine; Amino Sugars; Carbohydrate Conformation; Heptoses; Stereoisomerism; Sugar Acids; Gulo; Tetra
Año:2006
Volumen:341
Número:10
Página de inicio:1498
Página de fin:1504
DOI: http://dx.doi.org/10.1016/j.carres.2006.03.028
Título revista:Carbohydrate Research
Título revista abreviado:Carbohydr. Res.
ISSN:00086215
CODEN:CRBRA
CAS:acetone, 67-64-1; alanine, 56-41-7, 6898-94-8; azide, 12596-60-0, 14343-69-2; propane, 74-98-6; Alanine, 56-41-7; Amino Sugars; heptono-1,4-lactone; Heptoses; Sugar Acids
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00086215_v341_n10_p1498_Gomez

Referencias:

  • Okada, M., (2002) Prog. Polym. Sci., 27, pp. 87-133
  • Varela, O., Orgueira, H.A., (1999) Adv. Carbohydr. Chem. Biochem., 55, pp. 137-174
  • Törmälä, P., (1992) Adv. Mater., 4, pp. 589-591
  • Vainiopää, S., Rokkanen, P., Törmälä, P., (1989) Prog. Polym. Sci., 14, pp. 679-716
  • Gruner, S.A.W., Locardi, E., Lohof, E., Kessler, H., (2002) Chem. Rev., 102, pp. 491-514
  • Schweizer, F., (2002) Angew. Chem., Int. Ed., 41, pp. 230-253
  • van Well, R.M., Marinelli, L., Altona, C., Erkelens, K., Siegal, G., van Raaij, M., Llamas-Saiz, A.L., Overhand, M., (2003) J. Am. Chem. Soc., 125, pp. 10822-10829
  • Romero Zaliz, C.L., Varela, O., (2001) J. Carbohydr. Chem., 20, pp. 689-701
  • Romero Zaliz, C.L., Varela, O., (2003) Tetrahedron: Asymmetry, 14, pp. 2579-2586
  • Romero Zaliz, C.L., Varela, O., (2005) ARKIVOC, pp. 201-208
  • Romero Zaliz, C.L., Varela, O., (2005) Tetrahedron: Asymmetry, 16, pp. 97-103
  • Bueno, M., Galbis, J.A., García-Martín, M.G., de Paz, M.V., Zamora, F., Muñoz-Guerra, S., (1995) J. Polym. Sci., Part A: Polym. Chem., 33, pp. 299-305
  • Hunter, D.F.A., Fleet, G.W.J., (2003) Tetrahedron: Asymmetry, 14, pp. 3831-3839
  • Mayes, B.A., Stetz, R.J.E., Watterson, M.P., Edwards, A.A., Ansell, C.W.G., Tranter, G.E., Fleet, G.W.J., (2004) Tetrahedron: Asymmetry, 15, pp. 627-638
  • Zamora, F., Bueno, M., Molina, I., Orgueira, H.A., Varela, O., Galbis, J.A., (1996) Tetrahedron: Asymmetry, 7, pp. 1811-1818
  • Bueno, M., Zamora, F., Molina, I., Orgueira, H.A., Varela, O., Galbis, J.A., (1997) J. Polym. Sci., Part A: Polym. Chem., 55, pp. 3645-3653
  • Sparks, M.A., Williams, K.W., Whitesides, G.M., (1993) J. Med. Chem., 36, pp. 778-783
  • Jeroncic, L.O., Fernández Cirelli, A., Lederkremer, R.M., (1987) Carbohydr. Res., 167, pp. 175-186
  • Varela, O., Fernández Cirelli, A., Lederkremer, R.M., (1982) Carbohydr. Res., 100, pp. 424-430
  • Moradei, O., du Mortier, C., Varela, O., Lederkremer, R.M., (1991) J. Carbohydr. Chem., 10, pp. 469-479
  • Regeling, H., Rouville, E., Chittende, G.J.F., (1987) Recl. Trav. Chim. Pays-Bas, 106, pp. 461-464
  • Long, D.D., Stetz, R.J.E., Nash, R.J., Marquess, D.G., Lloyd, J.D., Winters, A.L., Asano, N., Fleet, G.W.J., (1999) J. Chem. Soc., Perkin Trans. 1, pp. 901-908
  • Horton, D., Varela, O., (1984) Carbohydr. Res., 134, pp. 205-214
  • Secrist III, J.A., Logue, M.W., (1972) J. Org. Chem., 37, pp. 335-336
  • Ramírez, F.J., Tuñón, I., Silla, E., (2004) Chem. Phys., 303, pp. 86-96
  • Vaino, A.R., Szarek, W.A., (2000) Adv. Carbohydr. Chem. Biochem., 56, pp. 44-50
  • Bose, A.K., Lal, B., (1973) Tetrahedron Lett., 40, pp. 3937-3940
  • Garegg, P.J., Samuelsson, B., (1979) J. Chem. Soc., Chem. Commun., pp. 978-980
  • Garegg, P.J., Samuelsson, B., (1980) J. Chem. Soc., Perkin Trans. 1, pp. 2866-2869
  • Garegg, P.J., Samuelsson, B., (1979) Synthesis, pp. 813-814

Citas:

---------- APA ----------
Gómez, R.V., Kolender, A.A. & Varela, O. (2006) . Synthesis of polyhydroxy amino acids based on d- and l-alanine from d-glycero-d-gulo-heptono-1,4-lactone. Carbohydrate Research, 341(10), 1498-1504.
http://dx.doi.org/10.1016/j.carres.2006.03.028
---------- CHICAGO ----------
Gómez, R.V., Kolender, A.A., Varela, O. "Synthesis of polyhydroxy amino acids based on d- and l-alanine from d-glycero-d-gulo-heptono-1,4-lactone" . Carbohydrate Research 341, no. 10 (2006) : 1498-1504.
http://dx.doi.org/10.1016/j.carres.2006.03.028
---------- MLA ----------
Gómez, R.V., Kolender, A.A., Varela, O. "Synthesis of polyhydroxy amino acids based on d- and l-alanine from d-glycero-d-gulo-heptono-1,4-lactone" . Carbohydrate Research, vol. 341, no. 10, 2006, pp. 1498-1504.
http://dx.doi.org/10.1016/j.carres.2006.03.028
---------- VANCOUVER ----------
Gómez, R.V., Kolender, A.A., Varela, O. Synthesis of polyhydroxy amino acids based on d- and l-alanine from d-glycero-d-gulo-heptono-1,4-lactone. Carbohydr. Res. 2006;341(10):1498-1504.
http://dx.doi.org/10.1016/j.carres.2006.03.028