Fragmentation of the Conjugate Base of 2-(1-Hydroxybenzyl)thiamin: Does Benzoylformate Decarboxylase Prevent Orbital Overlap to Avoid It?

Journal of the American Chemical Society

Volumn 126, Issue 1, 2004, Pages 68-69

  Hu, Qingyan ^a   Kluger, Ronald ^a  

^a UNIVERSITY OF TORONTO   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

2 (1 HYDROXYBENZYL)THIAMINE; BENZOYLFORMATE DECARBOXYLASE; CARBOXYLYASE; THIAMINE DERIVATIVE; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; DECARBOXYLATION; ELIMINATION REACTION; FRAGMENTATION REACTION; PROTON TRANSPORT;

EID: 0345868570     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0390505     Document Type: Article

References (26)

1. Ugai, T.; Tanaka, S.; Dokawa, S. J. Pharm. Soc. Jpn. 1943, 63, 269.
2. Ugai, T.; Dokawa, S.; Tsubokawa, S. J. Pharm. Soc. Jpn. 1944, 64, 3.
3. Mohrig, J. R.; Neckers, D. C. Laboratory Experiments in Organic Chemistry, 2nd ed.; Van Nostrand: New York, 1973.
4. Mieyal, J. J.; Votaw, R. G.; Krampilz, L. O.; Sable, H. Z. Biochim. Biophys. Acta 1967, 141, 205-8.
5. Mieyal, J. J.; Bantle, G.; Votaw, R. G.; Rosner, I. A.; Sable, H. Z. J. Biol. Chem. 1971, 246, 5213-9.
6. Dirmaier, L. J.; Garcia, G. A.; Kozarich, J. W.; Kenyon, G. L. J. Am. Chem. Soc. 1986, 108, 3149.
7. Hasson, M. S.; Muscate, A.; Henehan, G. T.; Guidinger, P. F.; Petsko, G. A.; Ringe, D.; Kenyon, G. L. Protein Sci. 1995. 4, 955-9.
8. Hasson, M. S.; Muscate, A.; McLeish, M. J.; Polovnikova, L. S.; Gerlt, J. A.; Kenyon, G. L.; Petsko, G. A.; Ringe, D. Biochemistry 1998, 37, 9918-9930.
9. Oka, Y.; Kishimoto, S.; Hirano, H. Chem. Pharm. Bull. 1970, 18, 527-33.
10. Kluger, R.; Lam, J. F.; Kim, C.-S. Bioorg. Chem. 1993, 21, 275-283.
11. Kluger, R.; Lam, J. F.; Pezacki, J. P.; Yang, C.-M. J. Am. Chem. Soc. 1995, 117, 11383-11389.
12. Kluger, R.; Moore, I. F. J. Am. Chem. Soc. 2000, 122, 6145-6150.
13. Moore, I. F.; Kluger, R. J. Am. Chem. Soc. 2002, 124, 1669-73.
14. Kluger, R. Pure Appl. Chem. 1997, 69, 1957-1967.
15. Hu, Q.; Kluger, R. J. Am. Chem. Soc. 2002, 124, 14858-9.
16. Zollewicz, J. A.; Baugh, T. D. Synthesis 1980, 217-18.
17. Kluger, R.; Chin, J.; Smyth, T. J. Am. Chem. Soc. 1981, 103, 884-8.
18. Weiss, P. M.; Garcia, G. A.; Kenyon, G. L.; Cleland, W. W.; Cook, P. F. Biochemistry 1988, 27, 2197-205.
19. Dunathan, H. C. Proc. Natl. Acad. Sci. U.S.A. 1966, 55, 712-6.
20. Washabaugh, M. W.; Jencks, W. P. J. Am. Chem. Soc. 1989, 111, 674-83.
21. Polovnikova, E. S.; McLeish, M. J.; Sergienko, E. A.; Burgner, J. T.; Anderson, N. L.; Bera, A. K.; Jordan, F.; Kenyon, G. L.; Hasson, M. S. Biochemistry 2003, 42, 1820-1830.
22. Wu, N.; Mo, Y.; Gao, J.; Pai, E. F. Proc. Natl. Acad. Sci. U.S.A. 2000, 97, 2017-2022.
23. Pletcher, J.; Sax, M.; Blank, G.; Wood, M. J. Am. Chem. Soc. 1977, 99, 1396-403.
24. Friedemann, R.; Breitkopf, C. Int. J. Quantum Chem. 1996, 57, 943-948.
25. Turano, A.; Furey, W.; Pletcher, J.; Sax, M.; Pike, D.; Kluger, R. J. Am. Chem. Soc. 1982, 104, 3089-3095.
26. Jencks, W. P. Adv. Enzymol. 1975, 43, 219-410.