(Hydroxyalkyl)cob(III)alamins as competitive inhibitors in coenzyme B12-dependent enzymic reactions: 1H-NMR structure analysis and kinetic studies with glycerol dehydratase and diol dehydratase

Helvetica Chimica Acta

Volumn 82, Issue 8, 1999, Pages 1250-1265

  Poppe, László ^a,b   Hull, William E ^c   Nitsche, Rainer ^a   Graf, Torsten ^a   Stupperich, Erhard ^d   Rétey, János ^a  

^a UNIVERSITY OF KARLSRUHE   (Germany)

^b CHEMICAL RESEARCH CENTER   (Hungary)

^c GERMAN CANCER RESEARCH CENTER DKFZ   (Germany)

^d UNIVERSITY OF ULM   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

APOENZYME; COBAMAMIDE; GLYCEROL; HYDROLYASE; HYDROXOCOBALAMIN; PROPYLENE GLYCOL;

ARTICLE; BINDING KINETICS; BINDING SITE; COMPETITIVE INHIBITION; DIASTEREOISOMER; ENTROPY; ENZYME MECHANISM; HYDROPHILICITY; PROTON NUCLEAR MAGNETIC RESONANCE; STRUCTURE ANALYSIS;

EID: 0032810968     PISSN: 0018019X     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1522-2675(19990804)82:8<1250::AID-HLCA1250>3.0.CO;2-I     Document Type: Article

References (43)

1. 'Vitamin B12', Eds. B. Zagalak, W. Friedrich, W. de Gruyter Verlag, Berlin-New York, 1979.
2. B. M. Babior, J. S. Krouwer, CRC Crit. Rev. Biochem. 1979, 6, 35.
3. B. T. Golding, in 'B12', Ed. D. Dolphin, John Wiley & Sons, New York, 1982, Vol. 1, pp. 543-582.
4. B. M. Babior, BioFactors 1988, 1, 21.
5. J. Rétey, in 'Chemical Aspects of Enzyme Biotechnology', Ed. T. O. Baldwin, Plenum Press, New York, 1990, p. 223.
6. C. D. Garr, J. M. Sirovatka, R. G. Finke, J. Am. Chem. Soc. 1996, 118, 11142.
7. C. D. Garr, R. G. Finke, Inorg. Chem. 1996, 35, 5912.
8. C. Luschinsky-Drennan, S. Huang, J. T. Drummond, R. G. Matthews, M. L. Ludwig, Science (Washington, D. C.) 1994, 266, 1669.
9. F. Mancia, N. H. Keep, A. Nakagawa, P. F. Leadlay, S. McSweeney, B. Rasmussen, P. Bösecke, O. Diat, P. R. Evans, Structure 1996, 4, 339.
10. E. Stupperich, H. J. Eisinger, S. P. J. Albracht, Eur. J. Biochem. 1990, 193, 105.
11. O. Zelder, B. Beatrix, F. Kroll, W. Buckel, FEBS Lett. 1995, 369, 252.
12. R. Padmakumar, S. Taoka, R. Padmakumar, R. Banerjee, J. Am. Chem. Soc. 1995, 117, 7033.
13. A. Abend, R. Nitsche, V. Bandarian, E. Stupperich, J. Rétey, Angew. Chem. 1998, 110, 643; ibid. Int. Ed. 1998, 37, 625.
14. A. Abend, R. Nitsche, V. Bandarian, E. Stupperich, J. Rétey, Angew. Chem. 1998, 110, 643; ibid. Int. Ed. 1998, 37, 625.
15. M. Yamanishi, S. Yamada, H. Muguruma, Y. Murakami, T. Tobimatsu, A. Ishida, J. Yamauchi, T. Toraya, Biochemistry 1998, 37, 4799.
16. C. C. Lawrence, G. J. Gerfen, V. Samano, R. Nitsche, M. J. Robins, J. Rétey, J. Stubbe, J. Biol. Chem. 1999, 274, 7039.
17. L. Poppe, E. Stupperich, W. E. Hull, T. Buckel, J. Rétey, Eur. J. Biochem. 1997, 250, 303.
18. L. Poppe, H. Bothe, G. Broeker, W. Buckel, E. Stupperich, J. Rétey, J. Mol. Catal. B, submitted.
19. O. Zelder, B. Beatrix, U. Leutbecher, W. Buckel, Eur. J. Biochem. 1994, 226, 577.
20. B. Beatrix, O. Zelder, W. Buckel, Eur. J. Biochem. 1994, 221, 101.
21. E. N. Marsh, N. McKie, N. K. Davis, P. F. Leadlay, Biochem. J. 1989, 260, 345.
22. R. Jansen, F. Kalousek, W. A. Fenton, L. E. Rosenberg, F. D. Ledley, Genomics 1989, 4, 198.
23. E. Andrews, R. Jansen, A. M. Crane, S. Cholin, D. McDonnell, F. D. Ledley, Biochem. Med. Metabol. Biol. 1993, 50, 135.
24. E. N. G. Marsh, D. E. Holloway, FEBS Lett. 1992, 310, 167.
25. T. Tobimatsu, T. Hara, M. Sakaguchi, Y. Kishimoto, Y. Wada, M. Isoda, T. Sakai, T. Toraya, J. Biol. Chem. 1995, 270, 7142.
26. M. Seyfried, R. Daniel, G. Gottschalk, J. Bacteriol. 1996, 178, 5793.
27. L. Poppe. J. Rétey, Eur. J. Biochem. 1997, 245, 398.
28. R. M. Dixon, B. T. Golding, O. W. Howarth, J. L. Murphy, J. Chem. Soc., Chem. Commun. 1983, 243.
29. N. W. Alcock, R. M. Dixon, B. T. Golding, J. Chem. Soc., Chem. Commun. 1985, 603.
30. L. Poppe, W. E. Hull, J. Rétey, Helv. Chim. Acta 1993, 76, 2367.
31. M. F. Summers, L. G. Marzilli, A. Bax, J. Am. Chem. Soc. 1986, 108, 4285.
32. T. G. Pagano, L. G. Marzilli, M. M. Flocco, C. Tsai, H. L. Carrel, J. P. Glusker, J. Am. Chem. Soc. 1991, 113, 531.
33. A. Bax, L. G. Marzilli, M. F. Summers, J. Am. Chem. Soc. 1987, 109, 566.
34. W. W. Bachovchin, R. G. Eagar, K. W. Moore, J. H. Richards, Biochemistry 1977, 16, 1082.
35. H. J. Böhm, G. Klebe, Angew. Chem. 1996, 108, 2750; ibid., Int. Ed. Engl. 1996, 35, 2588.
36. H. J. Böhm, G. Klebe, Angew. Chem. 1996, 108, 2750; ibid., Int. Ed. Engl. 1996, 35, 2588.
37. L. Poppe, L. Novák, M. Kajtár-Peredy, C. Szántay, Tetrahedron: Asymmetry 1993, 4, 2211.
38. E. Stupperich, H. Eisinger, Arch. Microbiol. 1989, 151, 372.
39. E. Stupperich, FEMS Microbiol. Rev. 1993, 12, 349.
40. V. Ya Bykhovskii, P. J. Santander, E. Stupperich, N. I. Zaitseva, M. A. Pusheva, E. N. Detkov, D. S. Valyushok, I. A. Scott, Appl. Biochem. Microbiol. 1996, 32, 179.
41. R. Daniel, G. Gottschalk, FEMS Microbiol. Lett. 1992, 100, 218.
42. P. G. Lenhert, Proc. Royal Soc. London, Ser. A 1968, 303, 45.
43. L. Poppe, J. Rétey, Arch. Biochem. Biophys. 1995, 316, 541.