D,L-S-methyllipoic acid methyl ester, a kinetically viable model for S- protonated lipoic acid as the oxidizing agent in reductive acyl transfers catalyzed by the 2-oxoacid dehydrogenase multienzyme complexes

Biochemistry

Volumn 37, Issue 5, 1998, Pages 1357-1364

  Pan, Ke ^a   Jordan, Frank ^a  

^a RUTGERS UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 OXOACID DEHYDROGENASE; FREE RADICAL; MERCURY DERIVATIVE; MULTIENZYME COMPLEX; OXIDIZING AGENT; SULFUR; THIAZOLE DERIVATIVE; THIOCTIC ACID;

ACYLATION; ARTICLE; CATALYSIS; ENZYME KINETICS; ENZYME MECHANISM; MOLECULAR INTERACTION; MOLECULAR MODEL; OXIDATION; PRIORITY JOURNAL; PROTON TRANSPORT;

ACYLATION; BICYCLO COMPOUNDS, HETEROCYCLIC; CATALYSIS; KINETICS; MAGNETIC RESONANCE SPECTROSCOPY; MESYLATES; MODELS, CHEMICAL; MULTIENZYME COMPLEXES; OXIDATION-REDUCTION; PROTEIN KINASES; THIOCTIC ACID;

EID: 0032477885     PISSN: 00062960     EISSN: None     Source Type: Journal    
DOI: 10.1021/bi971835y     Document Type: Article

References (29)

1. Reed, L. (1974) Acc. Chem. Res. 7, 40-46.
2. Perham, R. N. (1991) Biochemistry 30, 8501-8512.
3. Jordan, F., Kudzin, Z. H., and Rios, C. B. (1987) J. Am. Chem. Soc. 109, 4415-4416.
4. Bordwell, F. G., Satish, A. V., Rios, C. B., Chung, A., and Jordan, F. (1990) J. Am. Chem. Soc. 112, 792.
5. Barletta, G., Huskey, W. P., and Jordan, F. (1992) J. Am. Chem. Soc. 114, 7607-7608.
6. Barletta, G. L., Huskey, W. P., and Jordan, F. (1997) J. Am. Chem. Soc. 119, 2356-2362.
7. Barletta, G., Chung, A. C., Rios, C. B., Jordan, F., and Schlegel, J. M. (1990) J. Am. Chem. Soc. 112, 8144-8149.
8. Chiu, C. C., Pan, K., and Jordan, F. (1995) J. Am. Chem. Soc. 117, 7027-7028.
9. Chiu, C. C., Chung, A., Barletta, G., and Jordan, F. (1996) J. Am. Chem. Soc. 118, 11026-11029.
10. Frey, P. A., Flournoy, D. S., Gruys, K., and Yang, Y. S. (1989) Ann. N.Y. Acad. Sci. 373, 21-35.
11. Rastetter, W. H., Adams, J., Frost, J. W., Nummy, L. J., Frommer, J. E., and Roberts, K. B. (1979) J. Am. Chem. Soc. 101, 2752-2753.
12. Rastetter, W. H., and Adams, J. (1981) J. Org. Chem. 46, 1882-1883.
13. Smith, E. H. (1984) J. Chem. Soc., Perkin Trans. 1, 523-527.
14. Tazaki, M., Tanabe, H., Nagahama, S., and Takagi, M. (1994) J. Chem. Soc., Chem. Commun. 291-292.
15. Ravenscroft, M., Roberts, R. M., and Tillett, J. G. (1982) J. Chem. Soc., Perkin Trans. 2 1569-1572.
16. Chen, Y.-T., Barletta, G. L., Haghjoo, K., Cheng, J. T., and Jordan, F. (1994) J. Org. Chem. 59, 7714-7722.
17. Fava, A., Iliceto, A., and Camera, E. (1957) J. Am. Chem. Soc. 79, 833-838.
18. Hester, N. E., and Helmkamp, G. K. (1973) J. Org. Chem. 38, 461-464.
19. Caserio, M. C., Kim, J. K., Kahn, S. D., and Hehre, W. J. (1985) J. Am. Chem. Soc. 107, 2807-2809.
20. Caserio, M. C., and Kim, J. K. (1985) Phosphorus Sulfur Relat. Elem. 23, 169-195.
21. McNally, A., Motter, K., and Jordan, F. (1995) J. Biol. Chem. 270, 19736-19743.
22. Kice, J. L. (1968) Acc. Chem. Res. 1, 58-64.
23. Kice, J. L., and Ekmn, G. E. (1975) J. Org. Chem. 40, 711-716.
24. Pappas, J. A. (1977) J. Am. Chem. Soc. 99, 2926-2930.
25. Bach, R. D., and Rajan, S. J. (1979) J. Am. Chem. Soc. 101, 3112-3114.
26. Kim, J. K., Bonicamp, J., and Caserio, M. J. (1981) J. Org. Chem. 46, 4230-4236.
27. Streitwieser, A., Jr., and Heathcock, C. H. (1976) Introduction to Organic Chemistry, p 464, MacMillan Publishing Co., New York.
28. Creighton, T. E. (1993) Proteins-Structure and Molecular Properties, 2nd ed., p 395, W. H. Freeman and Co., New York.
29. Baburina, I., Moore, D. J., Volkov, A., Kahyaoglu, A., Jordan, F., and Mendelsohn, R.(1996) Biochemistry 35, 10249-10255.