Methylcorrinoids methylate radicals - Their second biological mode of action?

Angewandte Chemie - International Edition

Volumn 39, Issue 2, 2000, Pages 393-395

  Mosimann, Hervé ^a   Kräutler, Bernhard ^a  

^a UNIVERSITY OF INNSBRUCK   (Austria)

Author keywords

Cobalt; Methylations; Organometallic compounds; Radical reactions; Vitamin B12

Indexed keywords

CORRINOID; CYANOCOBALAMIN; MECOBALAMIN; METHIONINE SYNTHASE;

ARTICLE; ENZYME REGULATION; METHYLATION; REACTION ANALYSIS; THERMOSTABILITY;

EID: 0040735636     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(20000117)39:2<393::AID-ANIE393>3.0.CO;2-M     Document Type: Article

References (31)

1. 12 und verwandte Corrinoide. Vol. III/2 of Fermente, Hormone und Vitamine (Ed.: R. Ammon, W. Dirscherl), Georg Thieme, Stuttgart, 1975.
2. 12, Academic Press, New York, 1972.
3. 12 Proteins (Eds.: B. Kräutler, D. Arigoni, B. T. Golding), WILEY-VCH, Weinheim, 1998, pp. 3-43.
4. a) C. L. Drennan, S. Huang, J. T. Drummond, R. G. Matthews, M. L. Ludwig, Science 1994, 266, 1669-1674;
5. b) M. L. Ludwig, R. G. Matthews, Anun. Rev. Biochem. 1997, 66, 269-313.
6. 12 Proteins (Eds.: B. Kräutler, D. Arigoni, B. T. Golding), WILEY-VCH, Weinheim, 1998, pp. 447-458;
7. b) L. Kellenberger, D. Holmes, B. Martinoni, D. Arigoni, Chimia 1996, 50, 344.
8. a) D. R. Houck, K. Kobayashi, J. M. Williamson, H. G. Floss, J. Am. Chem. Soc. 1986, 108, 5365-5366;
9. b) P. Zhou, D. O'Hagan, U. Mocek, Z. Zeng, L.-D. Yuen, T. Frenzel, C. J. Unkefer, J. M. Beale, H. G. Floss, J. Am. Chem. Soc. 1989, 111, 7274-7276.
10. J. H. Grate, J. W. Grate, G. N. Schrauzer, J. Am. Chem. Soc. 1982, 104, 1588-1594.
11. M. Tollinger, T. Dérer, R. Konrat, B. Kräutler, J. Mol. Catal. A 1997, 116, 147-155.
12. 1H NMR).
13. +, which tends to decompose more than 100 times less rapidly than 2.
14. The NMR data provided no evidence for the existence of products derived from a rearrangement of 6 to a methylsuccinyl radical (for studies with 6 and with related radicals in solution, see S. Wollowitz, J. Halpern, J. Am. Chem. Soc. 1988, 110, 3112-3120).
15. B. D. Martin, R. G. Finke, J. Am. Chem. Soc. 1992, 114, 585-592.
16. G. N. Schrauzer, J. W. Sibert, R. J. Windgassen, J. Am. Chem. Soc. 1968, 90, 6681-6688.
17. [15]
18. A. J. Gordon, R. A. Ford in The Chemist's Companion, Wiley, New York, 1972.
19. J. F. Endicott, G. J. Ferraudi, J. Am. Chem. Soc. 1977, 99, 243-245.
20. J. C. Walton, Acc. Chem. Res. 1998, 31, 99-107.
21. M. D. Johnson, Acc. Chem. Res. 1983, 16, 343-349.
22. B. Kräutler, Helv. Chim. Acta 1987, 70, 1268-1278.
23. B. Kräutler, T. Dérer, P. Liu, W. Mühlecker, M. Puchberger, K. Gruber, C. Kratky, Angew. Chem. 1995, 107, 66-69; Angew. Chem. Int. Ed. Engl. 1995, 34, 84-86.
24. B. Kräutler, T. Dérer, P. Liu, W. Mühlecker, M. Puchberger, K. Gruber, C. Kratky, Angew. Chem. 1995, 107, 66-69; Angew. Chem. Int. Ed. Engl. 1995, 34, 84-86.
25. [13, 22] Our results suggest an alternative consideration, namely of a direct reaction of methyl radicals with the intact methylcorrinoid (1).
26. K. A. Rubinson, L. Itabashi, H. B. Mark, Jr., Inorg. Chem. 1982, 21, 3571-3573.
27. J. Halpern, Science 1985, 227, 869-875.
28. [3] then may act, in a complementary way, in homolytic demethylations of reactive (radicaloid) methylating agents.[8, 19]
29. a) Y. Murakami, Y. Hisaeda, T. Ozaki, T. Tashiro, T. Ohno, Y. Tani, Y. Matsuda, Bull. Chem. Soc. Jpn. 1987, 60, 311-324;
30. b) F. Björkling, J. Boutelje, S. Gatenbeck, K. Hult, T Norin, P. Szmulik, Tetrahedron 1985, 41, 1347-1352;
31. c) L. Kiriazis, E. Kalatzis, N. E. Alexandrou, J. Heterocycl. Chem. 1989, 26, 155-160.