A potent and highly selective inhibitor of human α-1,3-fucosyltransferase via click chemistry

Journal of the American Chemical Society

Volumn 125, Issue 32, 2003, Pages 9588-9589

  Lee, Lac V ^a   Mitchell, Michael L ^a   Huang, Shih Jung ^a   Fokin, Valery V ^a   Sharpless, K Barry ^a   Wong, Chi Huey ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALPHA 1,3 FUCOSYLTRANSFERASE; COPPER; ENZYME INHIBITOR; GUANYLATE KINASE; ISOENZYME; PYRUVATE KINASE; TRIAZOLE DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; DRUG EFFECT; ENZYME INHIBITION; IC 50; SYNTHESIS;

AZIDES; BINDING, COMPETITIVE; ENZYME INHIBITORS; FUCOSYLTRANSFERASES; GUANOSINE DIPHOSPHATE; HUMANS; HYDROPHOBICITY; KINETICS; SUBSTRATE SPECIFICITY; TRIAZOLES;

EID: 0042125393     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0302836     Document Type: Article

References (17)

1. (a) Staudacher, E. Trends Glycosci. Glycotechnol. 1996, 8, 391-408.
2. (b) Sears, P.; Wong, C.-H. Cell Mol. Life Sci. 1998, 54, 223-252.
3. Compain, P.; Martín, O. R. Bioorg. Med. Chem. 2001, 9, 3077-3092.
4. Qian, X.; Palcic, M. M. In Carbohydrates in Chemistry and Biology; Ernst, B., Ed.; Wiley-VCH Verlag GmbH: Weinheim, Germany, 2000; Vol. 3, pp 293-312.
5. Mitchell, M. L.; Tian, F.; Lee, L. V.; Wong, C.-H. Angew. Chem., Int. Ed. 2002, 41, 3041-3044.
6. Murray, B. W.; Takayma, S.; Schultz, J.; and Wong, C.-H. Biochemistry 1996, 35, 11183-11193.
7. Miura, Y.; Kim, S.; Etchison, J. R.; Ding, Y.; Hindsgaul, O.; and Freeze, H. Glycoconjugate J. 1999, 16, 725-730.
8. de Vries, T.; Palcic, M. P.; Schoenmakers, P. S.; van den Eijnden, D. H. ; and Joziasse, D. H. Glycobiology, 1997, 7, 921-927.
9. Kolb, H. C.; Finn, M. G.; and Sharpless, K. B. Angew. Chem., Int. Ed. 2001, 40, 2004-2021.
10. Lewis, W. G.; Green, L. G.; Grynszpan, F.; Radic, Z.; Carlier, P. R.; Taylor, P.; Finn, M. G.; and Sharpless, K. B. Angew. Chem., Int. Ed. 2002, 41, 1053-1057.
11. (a) Rostovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B. Angew. Chem., Int. Ed. 2002, 41, 2596-2599.
12. (b) Tornøe, C. W.; Christensen, C.; Meldal, M. J. Org. Chem. 2002, 67, 3057-3064.
13. Fazio, F.; Bryan, M. C.; Blixt, O.; Paulson, J. C.; Wong, C.-H. J. Am. Chem. Soc. 2002, 124, 14397-14402.
14. Mong, K.-K. T.; Lee, V. L.; Brown, J. R.; Esko, J. D.; Wong, C. H. Several LacNAc derivatives with different aglycons were prepared and tested, and it was found that the aglycon binding site for Fuc-T VI is hydrophobic.
15. de Vries, T.; Knegtel, R. M. A.; Holmes, E. H.; Macher, B. A. Glycobiology 2001, 11, 119R-128R.
16. 5 either mono- or bisubstrate analogue would produce the observed competitive (versus GDP-fucose) and noncompetitive (versus LacNAc or LacNAc-biphenyl) patterns.
17. Huisgen, R. In I,3-Dipolar Cycloaddition Chemistry; Padwa, A., Ed.; Wiley: New York, 1984; Chapter 1, pp 1-176.