Chemoenzymatic synthesis of the sialyl Lewis X glycan and its derivatives

Carbohydrate Research

Volumn 345, Issue 9, 2010, Pages 1107-1113

  Soriano del Amo, David ^a   Wang, Wei ^a   Besanceney, Christen ^a   Zheng, Tianqing ^a   He, Yizheng ^a   Gerwe, Brian ^a   Seidel III, Ronald D ^a   Wu, Peng ^a  

^a ALBERT EINSTEIN COLLEGE OF MEDICINE   (United States)

Author keywords

Chemoenzymatic synthesis; Fucose; Sialic acid; Transferases

Indexed keywords

CHEMO-ENZYMATIC SYNTHESIS; CO-FACTOR RECYCLING; DIPHOSPHATES; FACILE SYNTHESIS; FUCOSYLTRANSFERASES; IN-SITU; PYRUVATE KINASE; SIALIC ACIDS; SIALYL LEWIS X; TETRASACCHARIDES;

CARBOXYLIC ACIDS; ENZYMES;

ACIDS;

ALPHA 1,3 FUCOSYLTRANSFERASE; GLYCAN DERIVATIVE; GUANOSINE DIPHOSPHATE FUCOSE; PYRUVATE KINASE; SIALYL LEWIS X ANTIGEN; 5-ACETYLNEURAMINYL-(2-3)-GALACTOSYL-(1-4)-(FUCOPYRANOSYL-(1-3))-N-ACETYLGLUCOSAMINE; AMINOSUGAR; FUCOSE; FUCOSYLTRANSFERASE; GDP-L-FUCOSE PYROPHOSPHORYLASE; LACTOSAMINE; NUCLEOTIDYLTRANSFERASE; OLIGOSACCHARIDE;

ARTICLE; CARBOHYDRATE SYNTHESIS; ENZYME ACTIVITY; ENZYME SPECIFICITY; PRIORITY JOURNAL; CARBOHYDRATE ANALYSIS; CHEMISTRY; METABOLISM; MOLECULAR GENETICS; STEREOISOMERISM; SYNTHESIS;

AMINO SUGARS; CARBOHYDRATE SEQUENCE; FUCOSE; FUCOSYLTRANSFERASES; MOLECULAR SEQUENCE DATA; NUCLEOTIDYLTRANSFERASES; OLIGOSACCHARIDES; STEREOISOMERISM; SUBSTRATE SPECIFICITY;

EID: 77953139940     PISSN: 00086215     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.carres.2010.03.032     Document Type: Article

References (29)

1. Varki A., Cummings R.D., Esko J.D., Freeze H.H., Stanley P., Bertozzi C.R., Hart G.W., and Etzler M.E. Essentials of Glycobiology. 2nd ed. (2008), Cold Spring Harbor, New York
2. Phillips M.L., Nudelman E., Gaeta F.C., Perez M., Singhal A.K., Hakomori S., and Paulson J.C. Science 250 (1990) 1130-1132
3. Walz G., Aruffo A., Kolanus W., Bevilacqua M., and Seed B. Science 250 (1990) 1132-1135
4. Lowe J.B., Stoolman L.M., Nair R.P., Larsen R.D., Berhend T.L., and Marks R.M. Cell 63 (1990) 475-484
5. Simanek E.E., McGarvey G.J., Jablonowski J.A., and Wong C.H. Chem. Rev. 98 (1998) 833-862
6. Lapidot T., Dar A., and Kollet O. Blood 106 (2005) 1901-1910
7. Ichikawa Y., Lin Y.C., Dumas D.P., Shen G.J., Garciajunceda E., Williams M.A., Bayer R., Ketcham C., Walker L.E., Paulson J.C., and Wong C.H. J. Am. Chem. Soc. 114 (1992) 9283-9298
8. Ramphal J.Y., Zheng Z.L., Perez C., Walker L.E., DeFrees S.A., and Gaeta F.C. J. Med. Chem. 37 (1994) 3459-3463
9. x, see:. Kameyama A., Ishida H., Kiso M., and Hasegawa A. Carbohydr. Res. 209 (1991) c1-c4
10. Nicolaou K.C., Hummel C.W., Bockovich N.J., and Wong C.H. J. Chem. Soc., Chem. Commun. (1991) 870-872
11. Danishefsky S.J., Gervay J., Peterson J.M., Mcdonald F.E., Koseki K., Griffith D.A., Oriyama T., and Marsden S.P. J. Am. Chem. Soc. 117 (1995) 1940-1953
12. Yan L., and Kahne D. J. Am. Chem. Soc. 118 (1996) 9239-9248
13. Boltje T.J., Buskas T., and Boons G. Nat. Chem. 1 (2009) 611-622
14. Seeberger P.H. Nat. Chem. Biol. 5 (2009) 368-372
15. Hanson S., Best M., Bryan M.C., and Wong C.H. Trends Biochem. Sci. 29 (2004) 656-663
16. Ma B., Simala-Grant J.L., and Taylor D.E. Glycobiology 16 (2006) 158R-184R
17. Wang W., Hu T., Frantom P.A., Zheng T., Gerwe B., Soriano del Amo D., Garret S., Seidel III R.D., and Wu P. Natl. Acad. Sci. U.S.A. 106 (2009) 16096-16101
18. Coyne M.J., Reinap B., Lee M.M., and Comstock L.E. Science 307 (2005) 1778-1781
19. Yi W., Liu X., Li Y., Li J., Xia C., Zhou G., Zhang W., Zhao W., Chen X., and Wang P.G. Proc. Natl. Acad. Sci. U.S.A. 106 (2009) 4207-4212
20. Rabbani S., Miksa V., Wipf B., and Ernst B. Glycobiology 15 (2005) 1076-1083
21. Yu H., Chokhawala H.A., Huang S., and Chen X. Nat. Protoc. 1 (2006) 2485-2492
22. Yu H., Yu H., Karpel R., and Chen X. Bioorg. Med. Chem. 12 (2004) 6427-6435
23. Yu H., Chokhawala H., Karpel R., Yu H., Wu B., Zhang J., Zhang Y., Jia Q., and Chen X. J. Am. Chem. Soc. 127 (2005) 17618-17619
24. Baskin J.M., Prescher J.A., Laughlin S.T., Agard N.J., Chang P.V., Miller I.A., Lo A., Codelli J.A., and Bertozzi C.R. Proc. Natl. Acad. Sci. U.S.A. 104 (2007) 16793-16797
25. Feizi T., Fazio F., Chai W., and Wong C.H. Curr. Opin. Struct. Biol. 13 (2003) 637-645
26. Ichikawa Y., Wang R., and Wong C.H. Methods Enzymol. 247 (1994) 107-127
27. Stiller R., and Thiem J. Liebigs Ann. Chem. (1992) 467-471
28. Plowman K.M., and Krall A.R. Biochemistry 4 (1965) 2809-2814
29. Blixt O., Han S., Liao L., Zeng Y., Hoffmann J., Futakawa S., and Paulson J.C. J. Am. Chem. Soc. 130 (2008) 6680-6681