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Abstract:

β-(1→4)-Thiodisaccharides formed by a pentopyranose unit as reducing or non reducing end have been synthesized using a sugar enone derived from a hexose or pentose as Michael acceptor of a 1-thiopentopyranose or 1-thiohexopyranose derivatives. Thus, 2-propyl per-O-acetyl-3-deoxy-4-S-(β-d-Xylp)-4-thiohexopyranosid-2-ulose (3) and benzyl per-O-acetyl-3-deoxy-4-S-(β-d-Galp)-4-thiopentopyranosid-2-ulose (11) were obtained in almost quantitative yields. The carbonyl function of these uloses was reduced with NaBH4 or K-Selectride, and the stereochemical course of the reduction was highly dependent on the reaction temperature, reducing agent and solvent. Unexpectedly, reduction of 3 with NaBH4-THF at 0 °C gave a 3-deoxy-4-S-(β-d-Xylp)-4-thio-α-d-ribo-hexopyranoside derivative (6) as major product (74% yield), with isomerization of the sulfur-substituted C-4 stereocenter of the pyranone. Reduction of 11 gave always as major product the benzyl 3-deoxy-4-S-(Galp)-4-thio-β-d-threo-pentopyranoside derivative 14, which was the only product isolated (80% yield) in the reduction with K-Selectride in THF at -78 °C. Deprotection of 14 and its epimer at C-2 (13) afforded, respectively the free thiodisaccharides 19 and 18. They displayed strong inhibitory activity against the β-galactosidase from Escherichia coli. Thus, compound 18 proved to be a non-competitive inhibitor of the enzyme (Ki = 0.80 mM), whereas 19 was a mixed-type inhibitor (Ki = 32 μM). © 2009 Elsevier Ltd. All rights reserved.

Registro:

Documento: Artículo
Título:Synthesis of pentopyranosyl-containing thiodisaccharides. Inhibitory activity against β-glycosidases
Autor:Cagnoni, A.J.; Uhrig, M.L.; Varela, O.
Filiación:CIHIDECAR-CONICET, Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Pabellon 2, Ciudad Universitaria, 1428 Buenos Aires, Argentina
Palabras clave:Glycosidase inhibitors; Sugar enones; Thiodisaccharides; Thiopentopyranose; 2 propyl per o acetyl 3 deoxy 4 s (beta dextro xylopyranose) 4 thiohexopyranosid 2 ulose; benzyl per o acetyl 3 deoxy 4 s (beta dextro galactosylpyranose) 4 thiopentopyranosid 2 ulose; beta glucosidase; disaccharide; thiodisaccharide derivative; unclassified drug; article; concentration response; deprotection reaction; drug synthesis; enzyme inhibitor interaction; epimer; isomerization; reaction analysis; structure activity relation; beta-Galactosidase; beta-Glucosidase; Disaccharides; Enzyme Inhibitors; Stereoisomerism; Sulfhydryl Compounds; Temperature; Escherichia coli
Año:2009
Volumen:17
Número:17
Página de inicio:6203
Página de fin:6212
DOI: http://dx.doi.org/10.1016/j.bmc.2009.07.055
Título revista:Bioorganic and Medicinal Chemistry
Título revista abreviado:Bioorg. Med. Chem.
ISSN:09680896
CODEN:BMECE
CAS:beta glucosidase, 51683-43-3, 9001-22-3; Disaccharides; Enzyme Inhibitors; Sulfhydryl Compounds; beta-Galactosidase, 3.2.1.23; beta-Glucosidase, 3.2.1.21
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_09680896_v17_n17_p6203_Cagnoni

Referencias:

  • Davies, G.J., Gloster, T.M., Henrissat, B., (2005) Curr. Opin. Struct. Biol., 15, p. 637
  • Zechel, D.L., Withers, S.G., (2000) Acc. Chem. Res., 33, p. 11
  • Davies, G.J., Henrissat, B., (1995) Structure, 3, p. 853
  • McCarter, J.D., Withers, S.G., (1994) Curr. Opin. Struct. Biol., 4, p. 885
  • Cipolla, L., La Ferla, B., Gregori, M., (2006) Comb. Chem. High Throughput Screening, 9, p. 571
  • Asano, N., (2003) Glycobiology, 13, p. 93
  • Greimel, P., Spreitz, J., Stütz, A.E., Wrodnigg, T.M., (2003) Curr. Top. Med. Chem., 3, p. 513
  • Lohse, A., Hardlei, T., Jensen, A., Plesner, I.W., Bols, M., (2000) Biochem. J., 349, p. 211
  • Ratner, L., Heyden, N.V., Dedera, D., (1991) Virology, 181, p. 180
  • Gerber-Lemaire, S., Juillerat-Jeanneret, L., (2006) Mini-Rev. Med. Chem., 6, p. 1043
  • Paulsen, H., Brockhausen, I., (2001) Glycoconjugate J., 18, p. 867
  • Goss, P.E., Baker, M.A., Caarver, J.P., Dennis, J.W., (1995) Clin. Cancer Res., 1, p. 935
  • Witczak, Z.J., Culhane, J.M., (2005) Appl. Microbiol. Biotechnol., 69, p. 237
  • Witczak, Z.J., (1999) Curr. Med. Chem., 6, p. 165
  • Becker, B., Thimm, J., Thiem, J., (1996) J. Carbohydr. Chem., 15, p. 1179
  • Wen, X., Yuan, Y., Kuntz, D.A., Rose, D.R., Pinto, B.M., (2005) Biochemistry, 44, p. 6729
  • Witczak, Z.J., Kaplon, P., Dey, P.M., (2003) Carbohydr. Res., 338, p. 11
  • Kiefel, M.J., von Itzstein, M., (2002) Chem. Rev., 102, p. 471
  • Witczak, Z.J., Sun, J., Mielguj, R., (1995) Bioorg. Med. Chem. Lett., 5, p. 2169
  • Driguez, H., (2001) ChemBiochem., 2, p. 311
  • Driguez, H., (1997) Top. Curr. Chem., 187, p. 85
  • Szilágyi, L., Varela, O., (2006) Curr. Org. Chem., 10, p. 1745
  • Pachamuthu, K., Schmidt, R.R., (2006) Chem. Rev., 106, p. 160
  • Manzano, V.E., Uhrig, M.L., Varela, O., (2008) J. Org. Chem., 73, p. 7224
  • Uhrig, M.L., Manzano, V.E., Varela, O., (2006) Eur. J. Org. Chem., p. 162
  • Repetto, E., Marino, C., Uhrig, M.L., Varela, O., (2008) Eur. J. Org. Chem., 3, p. 540
  • Repetto, E., Marino, C., Uhrig, M.L., Varela, O., (2009) Bioorg. Med. Chem., 3, p. 540
  • Witczak, Z.J., Chhabra, R., Chen, H., Xie, X.-Q., (1997) Carbohydr. Res., 301, p. 167
  • Witczak, Z.J., Lorchak, D., Nguyen, N., (2007) Carbohydr. Res., 342, p. 1929
  • García-Herrero, A., Montero, E., Muñoz, J.L., Espinosa, J.F., Vián, A., García, J.L., Asensio, J.L., Jiménez-Barbero, J., (2002) J. Am. Chem. Soc., 124, p. 4804
  • Stanek, J., Šindlerova, M., Černý, M., (1965) Collect. Czech. Chem. Commun., 30, p. 297
  • De Fina, G., Varela, O., Lederkremer, R.M., (1988) Synthesis, p. 891
  • Horton, D., Priebe, W., Varela, O., (1986) J. Org. Chem., 51, p. 3479
  • Uhrig, M.L., Varela, O., (2002) Aust. J. Chem., 55, p. 155
  • Uhrig, M.L., Varela, O., (2002) Carbohydr. Res., 337, p. 2069
  • Henrissat, B., Hamer, G.K., Taylor, M.G., Marchessault, R.H., (2002) Can. J. Chem., 80, p. 1162
  • Uhrig, M.L., Varela, O., (2005) Synthesis, p. 893
  • Durette, P.L., Horton, D., (1971) J. Org. Chem., 36, p. 2658
  • Kolender, A.A., Matulewicz, M.C., (2002) Carbohydr. Res., 337, p. 57
  • Rivera-Sagredo, A., Fernández-Mayoralas, A., Jiménez-Barbero, J., Martín-Lomas, M., (1992) Carbohydr. Res., p. 129. , and references cited therein
  • Biely, P., (2003) Handbook of Food Enzymology, p. 879. , Whitaker J.R., Voragen A.G.J., and Wong D.W.S. (Eds), Marcel Dekker Inc., New York
  • Jänis, J., Hakanpää, J., Hakulinen, N., Ibatullin, F.M., Hoxha, A., Derrick, P.J., Rouvinen, J., Vainiotalo, P., (2005) FEBS J., 272, p. 2317
  • Ibatullin, F.M., Shabalin, K.A., Jänis, J.V., Shavva, A.G., (2003) Tetrahedron Lett., 44, p. 7961
  • Ibatullin, F.M., Shabalin, K.A., Jänis, J.V., Selivanov, S.I., (2001) Tetrahedron Lett., 42, p. 4565
  • Defaye, J., Guillot, J.-M., Biely, P., Vršanská, M., (1992) Carbohydr. Res., 228, p. 47
  • Dubost, E., Le Nouën, D., Streith, J., Tarnus, C., Tschamber, T., (2006) Eur. J. Org. Chem., p. 610
  • Jordan, D.B., Mertens, J.A., Braker, J.D., (2009) Biochim. Biophys. Acta, 1794, p. 144
  • Richard, J.P., (1998) Biochemistry, 37, p. 4305
  • Sinnot, M.L., (1990) Chem. Rev., 90, p. 1171
  • Griesser, H.W., Müller-Hill, B., Overath, P., (1983) Eur. J. Biochem., 137, p. 567
  • Matthews, B.W., (2005) C.R. Biol., 328, p. 549
  • Huber, R.E., Hlede, I.Y., Roth, N.J., McKenzie, K.C., Ghumman, K.K., (2001) Biochem. Cell. Biol., 79, p. 183
  • Gebler, J.C., Aebersold, R., Withers, S.G., (1992) J. Biol. Chem., 267, p. 11126
  • Cupples, C.G., Miller, J.H., Huber, R.E., (1990) J. Biol. Chem., 265, p. 5512
  • Juers, D.H., Heightman, T.D., Vasella, A., McCarter, J.D., Mackenzie, L., Withers, S.G., Matthews, B.W., (2001) Biochemistry, 40, p. 14781
  • Jacobson, R.H., Zhang, X.J., DuBose, R.F., Matthews, B.W., (1994) Nature, 369, p. 761
  • Sutendra, G., Wong, S., Fraser, M.E., Huber, R.E., (2007) Biochem. Biophys. Res. Commun., 352, p. 566
  • Espinosa, J.F., Montero, E., Vian, A., García, J.L., Dietrich, H., Schmidt, R.R., Martín-Lomas, M., Jiménez-Barbero, J., (1998) J. Am. Chem. Soc., 120, p. 1309
  • Steiner, A.J., Schitter, G., Stütz, A.E., Wrodnigg, T.M., Tarling, C.A., Withers, S.G., Fantur, K., Tropak, M., (2008) Bioorg. Med. Chem., 16, p. 10216

Citas:

---------- APA ----------
Cagnoni, A.J., Uhrig, M.L. & Varela, O. (2009) . Synthesis of pentopyranosyl-containing thiodisaccharides. Inhibitory activity against β-glycosidases. Bioorganic and Medicinal Chemistry, 17(17), 6203-6212.
http://dx.doi.org/10.1016/j.bmc.2009.07.055
---------- CHICAGO ----------
Cagnoni, A.J., Uhrig, M.L., Varela, O. "Synthesis of pentopyranosyl-containing thiodisaccharides. Inhibitory activity against β-glycosidases" . Bioorganic and Medicinal Chemistry 17, no. 17 (2009) : 6203-6212.
http://dx.doi.org/10.1016/j.bmc.2009.07.055
---------- MLA ----------
Cagnoni, A.J., Uhrig, M.L., Varela, O. "Synthesis of pentopyranosyl-containing thiodisaccharides. Inhibitory activity against β-glycosidases" . Bioorganic and Medicinal Chemistry, vol. 17, no. 17, 2009, pp. 6203-6212.
http://dx.doi.org/10.1016/j.bmc.2009.07.055
---------- VANCOUVER ----------
Cagnoni, A.J., Uhrig, M.L., Varela, O. Synthesis of pentopyranosyl-containing thiodisaccharides. Inhibitory activity against β-glycosidases. Bioorg. Med. Chem. 2009;17(17):6203-6212.
http://dx.doi.org/10.1016/j.bmc.2009.07.055