Synthesis of sugar-amino acid-nucleosides as potential glycosyltransferase inhibitors

Bioorganic and Medicinal Chemistry

Volumn 19, Issue 1, 2011, Pages 58-66

  Vembaiyan, Kannan ^a   Pearcey, Jean A ^b   Bhasin, Milan ^a   Lowary, Todd L ^b   Zou, Wei ^a  

^a NATIONAL RESEARCH COUNCIL CANADA   (Canada)

^b UNIVERSITY OF ALBERTA   (Canada)

Author keywords

Amino acid; C Glycoside; Galactosyltransferase; Inhibitors; Nucleoside; Synthesis

Indexed keywords

5' N [NALPHA (2,5 ANHYDRO GLUCIT 1 YL ACETAMIDO)HISTIDINAMIDO] 5' DEOXY URIDINE; 5' N [NALPHA (2,5 ANHYDRO GLUCIT 1 YL ACETAMIDO)TRYPTOPHANAMIDO] 5' DEOXY 6',7' DIHYDRO URIDINE; 5' N [NALPHA (2,5 ANHYDRO GLUCIT 1 YL ACETAMIDO)TRYPTOPHANAMIDO] 5' DEOXY URIDINE; 5' N [NALPHA (2,5 ANHYDRO MANNIT 1 YL ACETAMIDO) HISTIDINAMIDO] 5' DEOXY 6' ,7' DIHYDRO URIDINE; 5' N [NALPHA (2,5 ANHYDRO MANNIT 1 YL ACETAMIDO)HISTIDINAMIDO] 5' DEOXY 6',7' DIHYDRO URIDINE; 5' N [NALPHA (2,5 ANHYDRO MANNIT 1 YL ACETAMIDO)HISTIDINAMIDO] 5' DEOXY URIDINE; 5' N [NALPHA (2,5 ANHYDRO MANNIT 1 YL ACETAMIDO)TRYPTOPHANAMIDO] 5' DEOXY 6',7' DIHYDRO URIDINE; 5' N [NALPHA (2,5 ANHYDRO MANNIT 1 YL ACETAMIDO)TRYPTOPHANAMIDO] 5' DEOXY URIDINE; 5' N [NALPHA (2,6 ANHYDRO GLYCERO GLUCO HEPTIT 1 YL ACETAMIDO) LYSINAMIDO] 5' DEOXY URIDINE; 5' N [NALPHA (2,6 ANHYDRO GLYCERO GLUCO HEPTIT 1 YL ACETAMIDO)GLUTAMIDO] 5' DEOXY 6',7' DIHYDRO URIDINE; 5' N [NALPHA (2,6 ANHYDRO GLYCERO GLUCO HEPTIT 1 YL ACETAMIDO)GLUTAMIDO] 5' DEOXY URIDINE; 5' N [NALPHA (2,6 ANHYDRO GLYCERO GLUCO HEPTIT 1 YL ACETAMIDO)HISTIDINAMIDO] 5' DEOXY 60,70 DIHYDRO URIDINE; 5' N [NALPHA (2,6 ANHYDRO GLYCERO GLUCO HEPTIT 1 YL ACETAMIDO)HISTIDINAMIDO] 5' DEOXY URIDINE; 5' N [NALPHA (2,6 ANHYDRO GLYCERO GLUCO HEPTIT 1 YL ACETAMIDO)LYSINAMIDO] 5' DEOXY 6',7' DIHYDRO URIDINE; 5' N [NALPHA (2,6 ANHYDRO GLYCERO GLUCO HEPTIT 1 YL ACETAMIDO)TRYPTOPHANAMIDO] 5' DEOXY 6' ,7' DIHYDRO URIDINE; 5' N [NALPHA (2,6 ANHYDRO GLYCERO GLUCO HEPTIT 1 YL ACETAMIDO)TRYPTOPHANAMIDO] 5' DEOXY URIDINE; ETHAMBUTOL; GALACTAN; GLYCOSYLTRANSFERASE INHIBITOR; HISTIDINE; TRYPTOPHAN; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; BIOSYNTHESIS; CELL WALL; CONTROLLED STUDY; DRUG SYNTHESIS; ENZYME SUBSTRATE COMPLEX; LUNG ALVEOLUS MACROPHAGE; MEMBRANE TRANSPORT; MOUSE; MYCOBACTERIUM TUBERCULOSIS; NONHUMAN; STRUCTURE ACTIVITY RELATION;

AMINO ACIDS; CARBOHYDRATES; ENZYME INHIBITORS; GLYCOSYLTRANSFERASES; MAGNETIC RESONANCE SPECTROSCOPY; MASS SPECTROMETRY; MICROBIAL SENSITIVITY TESTS; MYCOBACTERIUM TUBERCULOSIS; NUCLEOSIDES;

MYCOBACTERIUM TUBERCULOSIS;

EID: 78650720514     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2010.11.044     Document Type: Article

References (33)

1. M.E. Taylor, and K. Drickamer Introduction to Glycobiology 2nd ed. 2006 Oxford University Press
2. A. Varki, R.D. Cummings, J.D. Esko, H.H. Freeze, P. Stanley, C.R. Bertozzi, G.W. Hart, and M.E. Etzler Essentials of Glycobiology 2nd ed. 2009 Cold Spring Harbor Laboratory Press
3. D. Horton The Development of Carbohydrate Chemistry and Biology H.G. Garg, M.K. Cowman, C.A. Hales, Carbohydrate Chemistry, Biology and Medical Applications 2008 Elsevier 1 28
4. Z. Fulton, A. McAlister, M.C.J. Wilce, R. Brammananth, L. Zaker-Tabrizi, M.A. Perugini, S.P. Bottomley, R.L. Coppel, P.K. Crellin, J. Rossjohn, and T. Beddoe J. Biol. Chem. 283 2008 27881
5. K. Persson, H.D. Ly, M. Dieckelmann, W.W. Wakarchuk, S.G. Withers, and N.C.J. Strynadka Nat. Struct. Biol. 8 2001 166
6. L. Lariviere, V. Gueguen-Chaignon, and S. Morera J. Mol. Biol. 330 2003 1077
7. L.C. Pedersen, T.A. Darden, and M. Negishi J. Biol. Chem. 277 2002 21869
8. P. Compain, and O.R. Martin Bioorg. Med. Chem. 9 2001 3077
9. K.-H. Jung, and R.R. Schmidt Glycosyltransferase Inhibitors C.-H. Wong, Carbohydrate-Based Drug Discovery 2003 Wiley-VCH Weiheim 609 660
10. W. Zou Curr. Top. Med. Chem. 14 2005 1363
11. F. Aman, C. Schaub, B. Muller, and R.R. Schmidt Chem. Eur. J. 4 1998 1106
12. C. Schaub, B. Muller, and R.R. Schmidt Glycoconjugate J. 15 1998 345
13. B. Muller, C. Schaub, and R.R. Schmidt Angew. Chem. Int. Ed. 37 1998 2893
14. R. Schworer, and R.R. Schmidt J. Am. Chem. Soc. 124 2002 1632
15. G. Carchon, F. Chretien, and Y. Chapleur Tetrahedron Lett. 44 2003 5715
16. G. Carchon, F. Chretien, P. Delannoy, A. Verbert, and Y. Chapleur Tetrahedron Lett. 42 2001 8821
17. J. Grugier, J. Xie, I. Duarte, and J.M. Valery J. Org. Chem. 65 2000 979
18. R. Wang, D.H. Steensma, Y. Takaoka, J.W. Yun, T. Kajimoto, and C.-H. Wong Bioorg. Med. Chem. 5 1997 661
19. L. Kremer, L.G. Dover, C. Morehouse, P. Hitchin, M. Everett, H.R. Morris, A. Dell, P.J. Brennan, M.R. McNeil, C. Flaherty, K. Duncan, and G.S. Besra J. Biol. Chem. 276 2001 26430
20. R.L. Rose, G.C. Completo, S.-J. Lin, M. McNeil, M.M. Palcic, and T.L. Lowary Am. Chem. Soc. 128 2006 6721
21. S.A.W. Gruner, L. Locardi, E. Lohof, and H. Kessler Chem. Rev. 102 2002 491
22. T.K. Chakraborty, P. Srinivasu, S. Tapadar, and B.K. Mohan Glycoconjugate J. 22 2005 83
23. P.E. Nielsen, M. Egholm, R.H. Berg, and O. Buchardt Science 254 1991 1497
24. P.E. Nielsen, M. Egholm, and O. Buchardt Bioconjugate Chem. 5 1994 3
25. P.E. Nielsen Curr. Opin. Biotechnol. 12 2001 16
26. P.E. Nielsen Chem. Biodiversity 7 2010 786
27. H. Rosemeyer Chem. Biodiversity 1 2004 361
28. A. Dondoni, A. Massi, and M. Aldhoun J. Org. Chem. 72 2007 7677
29. Z. Wang, H. Shao, E. Lacroix, S.-H. Wu, H. Jennings, and W. Zou J. Org. Chem. 68 2003 8097
30. J. Grugier, J. Xie, I. Duarte, and J.-M. Valéry J. Org. Chem. 65 2000 979
31. A. Bozzoli, W. Kazmierski, G. Kennedy, A. Pasquarello, and A. Pecunioso Bioorg. Med. Chem. Lett. 10 2000 2759
32. P. Arya, A. Barkley, and K.D. Randell J. Comb. Chem. 4 2002 193
33. N.L. Rose, R.B. Zheng, J. Pearcey, R. Zhou, G.C. Completo, and T.L. Lowary Carbohydr. Res. 343 2008 2130