But-3-ene-1,2-diol: A mechanism-based active site inhibitor for coenzyme B12-dependent glycerol dehydratase

ChemBioChem

Volumn 9, Issue 14, 2008, Pages 2268-2275

  Pierik, Antonio J ^a   Graf, Torsten ^b   Pemberton, Louise ^b   Golding, Bernard T ^c   Rétey, János ^b  

^a PHILIPPS UNIVERSITY MARBURG   (Germany)

^b UNIVERSITY OF KARLSRUHE   (Germany)

^c NEWCASTLE UNIVERSITY   (United Kingdom)

Author keywords

Cobalamins; EPR spectroscopy; Isotopes; Labeling; Radicals

Indexed keywords

BUT 3 ENE 1,2 DIOL; COBAMAMIDE; DEOXYADENOSINE; ENZYME INHIBITOR; GLYCEROL DEHYDRATASE; HYDROLYASE; PROPYLENE GLYCOL; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; COMPETITIVE INHIBITION; CONTROLLED STUDY; COVALENT BOND; ELECTRON SPIN RESONANCE; ENZYME ACTIVE SITE; ENZYME DENATURATION; ENZYME INHIBITION; ENZYME SUBSTRATE; ESCHERICHIA COLI; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL;

CATALYTIC DOMAIN; CITROBACTER FREUNDII; COBAMIDES; ELECTRON SPIN RESONANCE SPECTROSCOPY; ENZYME INHIBITORS; GLYCOLS; KINETICS; RECOMBINANT PROTEINS; STAINING AND LABELING; STEREOISOMERISM; SUGAR ALCOHOL DEHYDROGENASES; TIME FACTORS;

EID: 54349083595     PISSN: 14394227     EISSN: 14397633     Source Type: Journal    
DOI: 10.1002/cbic.200800213     Document Type: Article

References (50)

1. a) W. Buckel, B. T. Golding, Annu. Rev. Microbiol. 2006, 60, 27-49;
2. b) P. A. Frey, A. D. Hegemann, G. H. Reed, Chem. Rev. 2006, 106, 3302-3316.
3. a) G. Speranza, W. Buckel, B. T. Golding, J. Porphyrins Phthalocyanines 2004, 8, 290-300;
4. b) T. Toraya, Chem. Rev. 2003, 103, 2095-2127.
5. a) M. G. N. Hartmanis, T. C. Stadtman, Arch. Biochem. Biophys. 1986, 245, 144-152;
6. b) J. R. O'Brien, C. Raynaud, C. Croux, L. Girbal, P. Soucaille, W. N. Lanzilotta, Biochemistry 2004, 43, 4635-4645.
7. M. Emptage, S. Haynie, L. Laffend, J. Pucci, G. Whited, 2001 Patent Corporation Treaty (PCT) Int. App. WO1/12833A2.
8. P. A. Frey, G. L. Karabatsos, R. H. Abeles, Biochem. Biophys. Res. Commun. 1965, 18, 551-556.
9. J. Rétey, A. Umani-Ronchi, D. Arigoni, Experientia 1966, 22, 72-75.
10. a) B. T. Golding, T. J. Kemp, C. S. Sell, P. J. Sellars, W. P. Watson, J. Chem. Soc. Perkin Trans. 2 1978, 839-848;
11. b) B. T. Golding, C. S. Sell, P. J. Sellars, J. Chem. Soc. Perkin Trans. 2 1980, 961-970;
12. c) P. Müller, J. Rétey, J. Chem. Soc. Chem. Commun. 1983, 1342-134;
13. d) R. J. Anderson, S. Ashwell, I. Garnett, B. T. Golding, J. Chem. Soc. Perkin Trans. 1 2000, 4488-4498.
14. a) B. T. Golding, L. Radom, J. Am. Chem. Soc. 1976, 98, 6331-6338;
15. b) D. M. Smith, B. T. Golding, L. Radom, J. Am. Chem. Soc. 2001, 123, 1664-1675;
16. c) M. Eda, T. Kamachi, K. Yoshizawa, T. Toraya, Bull. Chem. Soc. Jpn. 2002, 75, 1469-1481;
17. d) T. Kamachi, T. Toraya, K. Yoshizawa, J. Am. Chem. Soc. 2004, 126, 16207-16216;
18. e) T. Kamachi, T. Toraya, K. Yoshizawa, Chem. Eur. J. 2007, 13, 7864-7873.
19. a) N. Shibata, J. Masuda, T. Tobimatsu, T. Toraya, K. Suto, Y. Morimoto, N. Yasuoka, Structure 1999, 7, 997-1008;
20. b) M. Yamanishi, M. Yunoki, T. Tobimatsu, H. Sato, J. Matsui, A. Dokiya, Y. Tuchi, K. Oek, K. Suto, N. Shibata, Y. Morimoto, N. Yasuoka, T. Toraya, Eur. J. Biochem. 2002, 269, 4484-4494;
21. c) N. Shibata, J. Masuda, Y. Morimoto, N. Yasuoka, T. Toraya, Biochemistry 2002, 41, 12607-12617
22. d) D. I. Liao, G. Dotson, I. Turner, L. Reiss. M. Emptage, J. Inorg. Biochem. 2003, 93, 84-91;
23. e) N. Shibata, Y. Nakanishi, M. Fukuoka, M. Yamanishi, N. Yasuoka, T. Toraya, J. Biol. Chem. 2003, 278, 22717-22725;
24. f) K. Kinoshita, M. Kawata, K. Ogura, A. Yamasaki, T. Watanabe, N. Komoto, N. Hieda, M. Yamanishi, T. Tobimatsu, T. Toraya, Biochemistry 2008, 47, 3162-3173.
25. a) J. Rétey, A. Umani-Ronchi, J. Seibl, D. Arigoni, Experientia 1966, 22, 502-504;
26. 12 (Eds.: B. Zagalak, W. Friedrich), de Gruyter, Berlin, 1979, pp. 389-410.
27. B. T. Golding, W. Buckel in Comprehensive Biological Catalysis (Ed.: M. L. Sinnott), Academic Press, London, 1997, pp. 239-259.
28. a) G. M. Sandala, D. M. Smith, M. L. Coote, B. T. Golding, L. Radom, J. Am. Chem. Soc. 2006, 128, 3433-3444;
29. b) D. J. Henry, C. J. Parkinson, P. M. Mayer, L. Radom, J. Phys. Chem. A 2001, 105, 6750-6756.
30. M. Seyfried, R. Daniel, G. Gottschalk, J. Bacteriol. 1996, 178, 5793-5796.
31. D. A. Howes, M. H. Brookes, D. Coates, B. T. Golding, A. T. Hudson, J. Chem. Res. (S) 1983, 9;
32. A. Howes, M. H. Brookes, D. Coates, B. T. Golding, A. T. Hudson, (M) 1983, 217-228.
33. N. Cheeseman, M. Fox, M. Jackson, I. C. Lennon, G. Meek, Proc. Natl. Acad. Sci. USA 2004, 101, 5396-5399; and references therein.
34. R. Dumont, H. P. Pfander, Helv. Chim. Acta 1983, 66, 814-823.
35. a) V. Aris, J. M. Brown, J. A. Conneely, B. T. Golding, D. H. Williamson, J. Chem. Soc. Perkin Trans. 2 1975, 4-10;
36. b) K. Takai, Y. Hotta, K. Oshima, H. Nozaki, Tetrahedron Lett. 1978, 19, 2417-2420.
37. S. C. Bergmeier, D. M. Stanchina, J. Org. Chem. 1999, 64, 2852-2859.
38. B. Furniss, A. J. Hannaford, V. Rogers, P. W. Smith, A. R. Tatchell, Vogel's Textbook of Practical Organic Chemistry, 4th ed., Longman, London 1978, pp. 338.
39. K. Ichimura, Bull. Chem. Soc. Jpn. 1970, 43, 2501-2506.
40. R. Nitsche, PhD Thesis, Universität Karlsruhe (Germany), 1999.
41. a) O. T. Magnusson, G. H. Reed, P. A. Frey, Biochemistry 2001, 40, 7773-7782;
42. b) S. O. Mansoorabadi, O. T. Magnusson, R. R. Poyner, P. A. Frey, G. H. Reed, Biochemistry 2006, 45, 14362-14370.
43. a) A. Abend, V. Bandarian, G. H. Reed, P. A. Frey, Biochemistry 2000, 39, 6250-6257;
44. b) P. Schwartz, R. LoBrutto, G. H. Reed, P. A. Frey, Helv. Chim. Acta 2003, 86, 3764-3775.
45. M. Yamanishi, H. Ide, Y. Murakami, T. Toraya, Biochemistry 2005, 44, 2113-2118; and references therein.
46. 12, Vol. 1 (Ed.: D. Dolphin), Wiley-Interscience, New York, 1982, Chapter 12, and references therein.
47. a) V. Bandarian, G. H. Reed, Biochemistry 1999, 38, 12394-12402;
48. b) G. E. Pake, J. Chem. Phys. 1948, 16, 327-336.
49. A. V. Rama Rao, D. Subhas Bose, M. K. Gurjar, T. Ravindranathan, Tetrahedron 1989, 45, 7031-7040.
50. U. Weigl, M. Heimberger, A. J. Pierik, J. Rétey, Chem. Eur. J. 2003, 9, 652-660.