Chemo-enzymatic synthesis of conformationally constrained oligosaccharides

Organic and Biomolecular Chemistry

Volumn 1, Issue 22, 2003, Pages 3891-3899

  Carmen Galan, M ^a   Venot, Andre P ^a   Glushka, John ^a   Imberty, Anne ^b   Boons, Geert Jan ^a  

^a UNIVERSITY OF GEORGIA   (United States)

^b CENTRE DE RECHERCHES SUR LES MACROMOLÉCULES VÉGÉTALES CERMAV CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ACYLATION; AMINES; COMPUTER SIMULATION; CONFORMATIONS; DERIVATIVES; ENZYMES; ETHERS; MOLECULAR DYNAMICS; RATE CONSTANTS; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

CHEMO ENZYMATIC SYNTHESIS; GLYCOSIDIC LINKAGE; METHYLENE AMIDE LINKER; MOLECULAR MECHANICS SIMULATION; N ACETLYLLACTOSAMINE; OLIGOSACCHARIDES; TRISACCHARIDES;

CARBOHYDRATES;

AMIDE; AMINOSUGAR; BETA D GALACTOSIDE ALPHA 2 6 SIALYLTRANSFERASE; BETA-D-GALACTOSIDE ALPHA 2-6-SIALYLTRANSFERASE; CARBENE; DRUG DERIVATIVE; FUCOSE; FUCOSYLTRANSFERASE; FUCOSYLTRANSFERASE V; GUANOSINE DIPHOSPHATE; HYDROCARBON; METHANE; N ACETYLLACTOSAMINE; N-ACETYLLACTOSAMINE; OLIGOSACCHARIDE; SIALYLTRANSFERASE; TRISACCHARIDE;

ANIMAL; ARTICLE; CARBOHYDRATE ANALYSIS; CHEMICAL MODEL; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; ENZYMOLOGY; LIVER; METABOLISM; MOLECULAR GENETICS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PROTEIN CONFORMATION; RAT; SYNTHESIS; THEORETICAL MODEL;

AMIDES; AMINO SUGARS; ANIMALS; CARBOHYDRATE CONFORMATION; CARBOHYDRATE SEQUENCE; FUCOSE; FUCOSYLTRANSFERASES; GUANOSINE DIPHOSPHATE; HYDROCARBONS; LIVER; MAGNETIC RESONANCE SPECTROSCOPY; METHANE; MODELS, CHEMICAL; MODELS, MOLECULAR; MODELS, THEORETICAL; MOLECULAR SEQUENCE DATA; OLIGOSACCHARIDES; PROTEIN CONFORMATION; RATS; SIALYLTRANSFERASES; TRISACCHARIDES;

EID: 0344946180     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b308559g     Document Type: Article

References (37)

1. A. Varki, Glycobiology, 1993, 3, 97-130.
2. R. A. Dwek, Chem. Rev., 1996, 96, 683-720.
3. S. W. Homans, Glycobiology, 1993, 3, 551-555.
4. A. Imberty and S. Perez, Chem. Rev., 2000, 100, 4567-4588.
5. C. F. Brewer and T. K. Dam, Chem. Rev., 2002, 102, 387.
6. J. P. Carver and D. A. Cumming, Pure Appl. Chem., 1987, 59, 1465-1476.
7. A. J. Petrescu, S. M. Petrescu, R. A. Dwek and M. R. Wormald, Glycobiology, 1999, 9, 343-352.
8. M. C. Galan, A. P. Venot, A. P. J. Glushka, A. Imberty and G. J. Boons, J. Am Chem. Soc., 2002, 124, 5964-5973.
9. D. R. Bundle, R. Alibes, S. Nilar, A. Otter, M. Warwas and P. Zhang, J. Am. Chem. Soc., 1998, 120, 5317-5318.
10. M. Wilstermann, J. Balogh and G. Magnusson, J. Org. Chem., 1997, 62, 3659-3665.
11. N. A. Navarre, A. van Oijen, A. Imberty, A. Poveda, J. Jimenez-Barbero, A. Cooper, M. A. Nutley and G. J. Boons, Chem. Eur. J., 1999, 5, 2281-2294.
12. M. J. Milton and D. R. Bundle, J. Am. Chem. Soc., 1998, 120, 10547-10548.
13. R. Alibes and D. R. Bundle, J. Org. Chem., 1998, 63, 6288-6301.
14. S. A. Wacowich-Sgarbi and D. R. Bundle, J. Org. Chem., 1999, 64, 9080-9089.
15. J. L. Koviach, M. D. Chappell and R. L. Halcomb, J. Org. Chem., 2001, 66, 2318-2326.
16. G. Thomas, J. L. Magnani, G. T. Patton, B. Ernst and W. Jahnke, Angew. Chem., Int. Ed., 2001, 40, 1941-1945.
17. A. Imberty, E. Mikros, J. Koca, R. Mollicone, R. Oriol and S. Pérez, Glycoconjugate J., 1995, 12, 331-349.
18. L. G. Baum and J. C. Paulson, Virology, 1991, 180, 10-15.
19. S. I. Hakomori, Adv. Cancer Res., 1989, 52, 257.
20. K. B. Wlasichuk, M. Kashem, P.V. Nikrad, P. Bird, C. Jiang and A. P. Venot, J. Biol. Chem., 1993, 268, 13971-13977.
21. T. de Vries, C. A. Srnca, M. M. Palcic, S. J. Sweidler, D. H. van den Eijnden and B. A. Macher, J. Biol. Chem., 1995, 270, 8712.
22. W. Dullenkopf, G. Ritter, S. Fortunato, L. J. Old and R. Schmidt, Chem. Eur. J., 1999, 5, 2432-2438.
23. E. Hounsell, Prog. Nucl. Magn. Reson. Spectrosc., 1995, 27, 445-474.
24. R. Williamson, B. Marquez, W. Gerwick and K. Kover, Magn. Reson. Chem., 2000, 38, 265-273.
25. I. Tvaroska, M. Hricovini and E. Petrakova, Carbohydr. Res., 1989, 189, 359-362.
26. S. A. Wacowich-Sgarbi, C. C. Ling, A. Otter and D. R. Bundle, J. Am. Chem. Soc., 2001, 123, 4362-4363.
27. K. Scott, J. Stonehous, J. Keeler, T.-L Hwang and A. J. Shaka, J. Am. Chem. Soc., 1995, 117, 4199-4200.
28. M. Martín Pastor, J. Felix-Espinosa, J. L. Asensio and J. Jiménez-Barbero, Carbohydr. Res., 1997, 298, 15-49.
29. Y. Kajihara, H. Kodama, T. Wakabayashi, K. Sato and H. Hashimoto, Carbohydr. Res., 1993, 247, 179-193.
30. G. J. Boons and A. V. Demchenko, Chem. Rev., 2000, 100, 4539.
31. V. Wittmann and C. H. Wong, J. Org. Chem., 1997, 62, 2144-2147.
32. M. Clark, R. D. I. Cramer and N. J. van den Opdenbosch, Comput. Chem., 1989, 10, 982-1012.
33. A. Imberty, E. Bettler, M. Karababa, K. Mazeau, P. Petrova and S. Pérez, in Perspectives in Structural Biology; Indian Academy of Sciences and Universities Press, Hyderabad, 1999, pp. 392-409.
34. S. Perez, K. Mazeau, A. Imberty, M. Karababa and E. Bettler, http://webenligne-cermav.cnrs.fr/databank/monosaccharides/index.html.
35. F. Delaglio, S. Grzesiek, G. Vuister, G. Zhu, J. Pfeifer and A. Bax, J. Biol. NMR, 1995, 6, 277-293.
36. J. Keeler, D. Neuhaus and J. J. Titman, Chem. Phys. Lett., 1988, 146, 545-548.
37. L. Poppe and H. van Halbeek, J. Magn. Reson., 1991, 93, 214-217.