Flavin catalyzed oxidations of sulfides and amines with molecular oxygen

Journal of the American Chemical Society

Volumn 125, Issue 10, 2003, Pages 2868-2869

  Imada, Yasushi ^a,b   Iida, Hiroki ^a,b   Ono, Satoshi ^a,b   Murahashi, Shun Ichi ^a,b  

^a OSAKA UNIVERSITY   (Japan)

^b OKAYAMA UNIVERSITY OF SCIENCE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; FLAVINE ADENINE NUCLEOTIDE; FLAVOPROTEIN; HYDRAZINE DERIVATIVE; MICROSOME ENZYME; OXYGEN; SULFIDE; TRIFLUOROETHANOL; UNSPECIFIC MONOOXYGENASE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; ENZYME METABOLISM; ENZYME SUBSTRATE; OXIDATION; REACTION TIME; SOLUBILITY; STOICHIOMETRY; XENOBIOTIC METABOLISM;

AMINES; CATALYSIS; FLAVINS; OXIDATION-REDUCTION; OXYGEN; OXYGENASES; SULFIDES;

EID: 0037433547     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja028276p     Document Type: Article

References (23)

1. (a) Wong, C.-H.; Whitesides, G. M. Enzymes in Synthetic Organic Chemistry; Tetrahedron Organic Chemistry Series; Pergamon: Oxford, 1994.
2. (b) Enzyme Catalysis in Organic Synthesis: Drauz, K., Waldmann, H., Eds.; VCH: Weinheim, 1995.
3. Murahashi, S.-I. Angew. Chem., Int. Ed. Engl. 1995, 34, 2443-2465.
4. (a) Dalko, P. I.; Moisan, L. Angew. Chem., Int. Ed. 2001, 40, 3726-3748.
5. (b) Adam, W.; Saha-Möller, C. R.; Ganeshpure, P. A. Chem. Rev. 2001, 101, 3499-3548.
6. Hill, C. L. Nature 1999, 401, 436-437.
7. Chemistry and Biochemistry of Flavoenzymes; Müller, F., Ed.; CRC Press: Boston, 1991.
8. Poulsen, L. L.; Ziegler, D. M. J. Biol. Chem. 1979, 254, 6449-6455.
9. Kemal, C.; Bruice, T. C. Proc. Natl. Acad. Sci. U.S.A. 1976, 73, 995-999.
10. Ball, S.; Bruice, T. C. J. Am. Chem. Soc. 1979, 101, 4017-4019.
11. Murahashi, S.-I.; Oda, T.; Masui, Y. J. Am. Chem. Soc. 1989, 111, 5002-5003.
12. Bergstad, K.; Bäckvall, J. E. J. Org. Chem. 1998, 63, 6650-6655.
13. Bergstad, K.; Jonsson, S. Y.; Bäckvall, J. E. J. Am. Chem. Soc. 1999, 121, 10424-10425.
14. Minidis, A. B. E.; Bäckvall, J. E. Chem.-Eur. J. 2001, 7, 297-302.
15. Mazzini, C.; Lebreton, J.; Furstoss, R. J. Org. Chem. 1996, 61, 8-9.
16. Murahashi, S.-I.; Ono, S.; Imada, Y. Angew. Chem., Int. Ed. 2002, 41, 2366-2368.
17. Kamel, C.; Chan, T. W.; Bruice, T. C. J. Am. Chem. Soc. 1977, 99, 7272-7286.
18. Patek, D. R.; Hellerman, L. J. Biol. Chem. 1974, 249, 2373-2380.
19. Brink, G. J. t.; Vis, J. M.; Arends, I. W. C. E.; Sheldon, R. A. J. Org. Chem. 2001, 66, 2429-2433.
20. Sánchez, M. A.; Mainar, A. M.; Pardo, J. I.; López, M. C.; Urieta, J. S. Can. J. Chem. 2001, 79, 1460-1465.
21. For enantioselective catalytic electrophilic addition reactions, see: (a) Murahashi, S.-I.; Tsuji, T.; Ito, S. Chem. Commun. 2000, 409-410. (b) Murahashi, S.-I.; Imada, Y.; Kawakami, T.; Harada, K.; Yonemushi. Y.; Tomita. N. J. Am. Chem. Soc. 2002, 124, 2888-2889.
22. For enantioselective catalytic electrophilic addition reactions, see: (a) Murahashi, S.-I.; Tsuji, T.; Ito, S. Chem. Commun. 2000, 409-410. (b) Murahashi, S.-I.; Imada, Y.; Kawakami, T.; Harada, K.; Yonemushi, Y.; Tomita. N. J. Am. Chem. Soc. 2002, 124, 2888-2889.
23. Oae, S.; Asada, K.; Yoshimura, T. Tetrahedron Lett. 1983, 24, 1265-1268.