Mechanism of action of vitamin B12. A new test for free radical intermediates using a cyclopropane model for the methylmalonyl-CoA to succinyl-CoA carbon skeleton rearrangement

Journal of the American Chemical Society

Volumn 118, Issue 3, 1996, Pages 711-

  He, Mu ^a   Dowd, Paul ^a  

^a UNIVERSITY OF PITTSBURGH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYANOCOBALAMIN; CYCLOPROPANE DERIVATIVE; SUCCINIC ACID DERIVATIVE;

ARTICLE; DRUG MECHANISM; ENZYME ACTIVITY; MODEL; REACTION ANALYSIS; SPECTROPHOTOMETRY;

EID: 0030031803     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9532401     Document Type: Article

References (19)

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6. For examples, see: Griller, D.; Ingold, K. U. Acc. Chem. Res. 1980, 13, 317-323. Bowry, V. W.; Lusztyk, J.; Ingold, K. U. J. Am. Chem. Soc. 1989, 111, 1927-1928. Bowry, V. W.; Lusztyk, J.; Ingold, K. U. J. Am. Chem. Soc. 1991, 113, 5687-5698. Newcomb, M.; Johnson, C. C.; Manek, M. B.; Varick, T. R. J. Am. Chem. Soc. 1992, 114, 10915-10921. Newcomb, M. Tetrahedron 1993, 49, 1151-1176. Ortiz de Montellano, P. R.; Stearns, R. A. J. Am. Chem. Soc. 1987, 109, 3415-3420. Bowry, V. W.; Ingold, K. U. J. Am. Chem. Soc. 1991, 113, 5699-5707. Liu, K. E.; Johnson, C. C.; Newcomb, M.; Lippard, S. J. J. Am. Chem. Soc. 1993, 115, 939-947. Inchley, P.; Lindsay Smith, J. R.; Lower, R. J. Nouv. J. Chim. 1989, 132, 669-676. Atkinson, J. K.; Ingold, K. U. Biochemistry 1993, 32, 9209-9214.
7. For examples, see: Griller, D.; Ingold, K. U. Acc. Chem. Res. 1980, 13, 317-323. Bowry, V. W.; Lusztyk, J.; Ingold, K. U. J. Am. Chem. Soc. 1989, 111, 1927-1928. Bowry, V. W.; Lusztyk, J.; Ingold, K. U. J. Am. Chem. Soc. 1991, 113, 5687-5698. Newcomb, M.; Johnson, C. C.; Manek, M. B.; Varick, T. R. J. Am. Chem. Soc. 1992, 114, 10915-10921. Newcomb, M. Tetrahedron 1993, 49, 1151-1176. Ortiz de Montellano, P. R.; Stearns, R. A. J. Am. Chem. Soc. 1987, 109, 3415-3420. Bowry, V. W.; Ingold, K. U. J. Am. Chem. Soc. 1991, 113, 5699-5707. Liu, K. E.; Johnson, C. C.; Newcomb, M.; Lippard, S. J. J. Am. Chem. Soc. 1993, 115, 939-947. Inchley, P.; Lindsay Smith, J. R.; Lower, R. J. Nouv. J. Chim. 1989, 132, 669-676. Atkinson, J. K.; Ingold, K. U. Biochemistry 1993, 32, 9209-9214.
8. For examples, see: Griller, D.; Ingold, K. U. Acc. Chem. Res. 1980, 13, 317-323. Bowry, V. W.; Lusztyk, J.; Ingold, K. U. J. Am. Chem. Soc. 1989, 111, 1927-1928. Bowry, V. W.; Lusztyk, J.; Ingold, K. U. J. Am. Chem. Soc. 1991, 113, 5687-5698. Newcomb, M.; Johnson, C. C.; Manek, M. B.; Varick, T. R. J. Am. Chem. Soc. 1992, 114, 10915-10921. Newcomb, M. Tetrahedron 1993, 49, 1151-1176. Ortiz de Montellano, P. R.; Stearns, R. A. J. Am. Chem. Soc. 1987, 109, 3415-3420. Bowry, V. W.; Ingold, K. U. J. Am. Chem. Soc. 1991, 113, 5699-5707. Liu, K. E.; Johnson, C. C.; Newcomb, M.; Lippard, S. J. J. Am. Chem. Soc. 1993, 115, 939-947. Inchley, P.; Lindsay Smith, J. R.; Lower, R. J. Nouv. J. Chim. 1989, 132, 669-676. Atkinson, J. K.; Ingold, K. U. Biochemistry 1993, 32, 9209-9214.
9. For examples, see: Griller, D.; Ingold, K. U. Acc. Chem. Res. 1980, 13, 317-323. Bowry, V. W.; Lusztyk, J.; Ingold, K. U. J. Am. Chem. Soc. 1989, 111, 1927-1928. Bowry, V. W.; Lusztyk, J.; Ingold, K. U. J. Am. Chem. Soc. 1991, 113, 5687-5698. Newcomb, M.; Johnson, C. C.; Manek, M. B.; Varick, T. R. J. Am. Chem. Soc. 1992, 114, 10915-10921. Newcomb, M. Tetrahedron 1993, 49, 1151-1176. Ortiz de Montellano, P. R.; Stearns, R. A. J. Am. Chem. Soc. 1987, 109, 3415-3420. Bowry, V. W.; Ingold, K. U. J. Am. Chem. Soc. 1991, 113, 5699-5707. Liu, K. E.; Johnson, C. C.; Newcomb, M.; Lippard, S. J. J. Am. Chem. Soc. 1993, 115, 939-947. Inchley, P.; Lindsay Smith, J. R.; Lower, R. J. Nouv. J. Chim. 1989, 132, 669-676. Atkinson, J. K.; Ingold, K. U. Biochemistry 1993, 32, 9209-9214.
10. For examples, see: Griller, D.; Ingold, K. U. Acc. Chem. Res. 1980, 13, 317-323. Bowry, V. W.; Lusztyk, J.; Ingold, K. U. J. Am. Chem. Soc. 1989, 111, 1927-1928. Bowry, V. W.; Lusztyk, J.; Ingold, K. U. J. Am. Chem. Soc. 1991, 113, 5687-5698. Newcomb, M.; Johnson, C. C.; Manek, M. B.; Varick, T. R. J. Am. Chem. Soc. 1992, 114, 10915-10921. Newcomb, M. Tetrahedron 1993, 49, 1151-1176. Ortiz de Montellano, P. R.; Stearns, R. A. J. Am. Chem. Soc. 1987, 109, 3415-3420. Bowry, V. W.; Ingold, K. U. J. Am. Chem. Soc. 1991, 113, 5699-5707. Liu, K. E.; Johnson, C. C.; Newcomb, M.; Lippard, S. J. J. Am. Chem. Soc. 1993, 115, 939-947. Inchley, P.; Lindsay Smith, J. R.; Lower, R. J. Nouv. J. Chim. 1989, 132, 669-676. Atkinson, J. K.; Ingold, K. U. Biochemistry 1993, 32, 9209-9214.
11. For examples, see: Griller, D.; Ingold, K. U. Acc. Chem. Res. 1980, 13, 317-323. Bowry, V. W.; Lusztyk, J.; Ingold, K. U. J. Am. Chem. Soc. 1989, 111, 1927-1928. Bowry, V. W.; Lusztyk, J.; Ingold, K. U. J. Am. Chem. Soc. 1991, 113, 5687-5698. Newcomb, M.; Johnson, C. C.; Manek, M. B.; Varick, T. R. J. Am. Chem. Soc. 1992, 114, 10915-10921. Newcomb, M. Tetrahedron 1993, 49, 1151-1176. Ortiz de Montellano, P. R.; Stearns, R. A. J. Am. Chem. Soc. 1987, 109, 3415-3420. Bowry, V. W.; Ingold, K. U. J. Am. Chem. Soc. 1991, 113, 5699-5707. Liu, K. E.; Johnson, C. C.; Newcomb, M.; Lippard, S. J. J. Am. Chem. Soc. 1993, 115, 939-947. Inchley, P.; Lindsay Smith, J. R.; Lower, R. J. Nouv. J. Chim. 1989, 132, 669-676. Atkinson, J. K.; Ingold, K. U. Biochemistry 1993, 32, 9209-9214.
12. For examples, see: Griller, D.; Ingold, K. U. Acc. Chem. Res. 1980, 13, 317-323. Bowry, V. W.; Lusztyk, J.; Ingold, K. U. J. Am. Chem. Soc. 1989, 111, 1927-1928. Bowry, V. W.; Lusztyk, J.; Ingold, K. U. J. Am. Chem. Soc. 1991, 113, 5687-5698. Newcomb, M.; Johnson, C. C.; Manek, M. B.; Varick, T. R. J. Am. Chem. Soc. 1992, 114, 10915-10921. Newcomb, M. Tetrahedron 1993, 49, 1151-1176. Ortiz de Montellano, P. R.; Stearns, R. A. J. Am. Chem. Soc. 1987, 109, 3415-3420. Bowry, V. W.; Ingold, K. U. J. Am. Chem. Soc. 1991, 113, 5699-5707. Liu, K. E.; Johnson, C. C.; Newcomb, M.; Lippard, S. J. J. Am. Chem. Soc. 1993, 115, 939-947. Inchley, P.; Lindsay Smith, J. R.; Lower, R. J. Nouv. J. Chim. 1989, 132, 669-676. Atkinson, J. K.; Ingold, K. U. Biochemistry 1993, 32, 9209-9214.
13. The product isolated was the diethyl ester, reasonably presumed to arise from exchange of the thioester with solvent following rearrangement.
14. Cf.; Scott, A. I.; Kang, K. J. Am. Chem. Soc. 1977, 99, 1997-1999. Scott, A. I.; Kang, J.; Dalton, D.; Chung, S. K. J. Am. Chem. Soc. 1978, 100, 3603-3604. Scott, A. I.; Kang, J.; Dowd, P.; Trivedi, B. K. Bioorg. Chem. 1980, 9, 227-230.
15. Cf.; Scott, A. I.; Kang, K. J. Am. Chem. Soc. 1977, 99, 1997-1999. Scott, A. I.; Kang, J.; Dalton, D.; Chung, S. K. J. Am. Chem. Soc. 1978, 100, 3603-3604. Scott, A. I.; Kang, J.; Dowd, P.; Trivedi, B. K. Bioorg. Chem. 1980, 9, 227-230.
16. Cf.; Scott, A. I.; Kang, K. J. Am. Chem. Soc. 1977, 99, 1997-1999. Scott, A. I.; Kang, J.; Dalton, D.; Chung, S. K. J. Am. Chem. Soc. 1978, 100, 3603-3604. Scott, A. I.; Kang, J.; Dowd, P.; Trivedi, B. K. Bioorg. Chem. 1980, 9, 227-230.
17. Alternatively, the reaction of 1 → 2 may proceed through an electron transfer sequence.
18. Beckwith, A. L. J.; Bowry, V. W. J. Am. Chem. Soc. 1994, 116, 2710-2716.
19. See footnote 30 in the following: Newcomb, M.; Horner, J. H.; Filipkowski, M. A.; Ha, C.; Park, S.-U. J. Am. Chem. Soc. 1995, 117, 3674-3684.