Structure and conformation of mannoamidines by NMR and molecular modeling: Are they good transition state mimics?

Journal of Carbohydrate Chemistry

Volumn 15, Issue 8, 1996, Pages 985-1000

  Blériot, Yves ^a,c   Genre Grandpierre, Arnaud ^a   Imberty, Anne ^b   Tellier, Charles ^a  

^a U de Recherche sur la Biocatalyse   (France)

^b Centre National de la Recherche Scientifique   (France)

^c UNIVERSITY OF OXFORD   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0030496714     PISSN: 07328303     EISSN: None     Source Type: Journal    
DOI: 10.1080/07328309608005704     Document Type: Article

References (29)

1. a) M.K. Tong, G. Papandreou, and B. Ganem, J. Am. Chem. Soc., 112, 6137 (1990);
2. b) B. Ganem and G. Papandreou, J. Am. Chem. Soc., 113, 8984 (1991);
3. c) G. Papandreou, M.K. Tong and B. Ganem, J. Am. Chem. Soc., 115, 11682 (1993).
4. a) Y.T. Pan, G.P. Kaushal, G. Papandreou, B. Ganem and A.D. Elbein, J. Biol. Chem., 267, 8313 (1992);
5. b) Y. Blériot, T. Dintinger, A. Genre-Grandpierre, M. Padrines and C. Tellier, Bioorg. Med. Chem. Lett., 5, 2655 (1995).
6. a) M.L. Sinnott, Chem. Rev., 90, 1171 (1990);
7. b) G. Legler, Adv. Carbohydr. Chem. Biochem. 48, 319 (1990).
8. J. Yu, L.C. Hsieh. L. Kochersperger, S. Yonkovich, J. Stephans, M.A. Gallop and P.G. Schultz, Angew.Chem. Int. Ed. Engl., 33, 339 (1994).
9. R.A. Lerner, S.J. Benkovic and P.G. Schultz, Science, 252, 659 (1995) and references cited.
10. Y. Blériot, A. Genre-Grandpierre, and C. Tellier, Tetrahedron Lett., 35, 1867 (1994).
11. Y. Blériot, T. Dintinger, N. Guillo and C. Tellier, Tetrahedron Lett., 36, 5175 (1995).
12. M.J.S. Dewar, E.G. Zoebisch, E.F. Healy and J.P.P. Stewart, J. Am. Chem. Soc., 107, 3902 (1985).
13. Y. Blériot, PhD Thesis, Nantes, France (1994).
14. J. Oszczapowicz, in The Chemistry of Amidines and Imidates, S. Patai and Z. Rappoport, Eds., Wiley, New York (1991).
15. C.L. Perrin, in The Chemistry of Amidines and Imidates, S. Patai and Z. Rappoport, Eds., Wiley, New York (1991).
16. C.A.G. Haasnoot, F.A.A.M. De Leeuw and C. Altona, Tetrahedron, 36, 2783 (1980).
17. a) I. Tvaroska and J-P. Graver, J. Chem. Res., Miniprint, 123 (1991);
18. b) S.E. Barrows, F.J. Dulles, C.J. Cramer, A.D. French and D.G. Truhlar, Carbohydr. Res., 276, 219 (1995).
19. C. Hervé du Penhoat, A. Imberty, N. Roques, V. Michon, J. Mentech, G. Descotes and S. Pérez, J. Am. Chem. Soc., 113, 3720 (1991).
20. A. Imberty, S. Gerber, V. Tran and S. Pérez, Glycoconjugate J., 7, 27 (1990).
21. A. Imberty, V. Tran and S. Pérez, J. Comput. Chem., 11, 205 (1989).
22. P.A. Bartlett and C.K. Marlowe, Biochemistry, 22, 4618 (1983).
23. M.A. Phillips, A.P. Kaplan, W.J. Rutter and P.A. Bartlett, Biochemistry, 31, 959 (1992).
24. P. Ermert, A. Vasella, M. Weber, K. Rupitz and S. Withers, Carbohydr. Res., 250, 113 (1993).
25. R.J. Woods, C. W. Andrews and P. Bowen, J. Am. Chem. Soc., 114, 859 (1992).
26. Atlas of Protein Side Chain Interaction, J. Singh and J.M. Thornton, Eds., IRL Press, Oxford (1992)
27. T.M. Jespersen, M. Bols, M.R. Sierks and T. Skrydstrup, Tetrahedron, 50, 13449 (1994).
28. Spartan 4.0, Wavefunction, Inc., 18401 Von Karman Ave, #370, Irvine, CA 92715, USA.
29. P. Deslongchamps, Y.L. Dory and S. Li, Can. J. Chem., 72, 2021 (1994).