Cytochrome P-450 model reactions: Efficient and highly selective oxidation of alcohols with tetrabutylammonium peroxymonosulfate catalyzed by Mn-porphyrins

Bioorganic and Medicinal Chemistry

Volumn 15, Issue 8, 2007, Pages 3097-3101

  Rezaeifard, Abdolreza ^a   Jafarpour, Maasoumeh ^a   Moghaddam, Gholamreza Kardan ^a   Amini, Fatemeh ^a  

^a UNIVERSITY OF BIRJAND   (Iran)

Author keywords

Alcohol; Aldehyde; Ketone; Mn porphyrin; Oxidation; Tetrabutylammonium peroxymonosulfate

Indexed keywords

ALDEHYDE; ALKANOL; ALLYL COMPOUND; BENZYL ALCOHOL; CYTOCHROME P450; KETONE; MANGANESE; PYRIDINE; TETRABUTYLAMMONIUM; TETRABUTYLAMMONIUM PEROXYMONOSULFATE; TETRAPHENYLPORPHYRIN; UNCLASSIFIED DRUG;

ALCOHOL OXIDATION; ARTICLE; BIOMIMETICS; CATALYSIS; ELECTRON; ENZYME MECHANISM; TURNOVER TIME;

ALCOHOLS; ALDEHYDES; CATALYSIS; CYTOCHROME P-450 ENZYME SYSTEM; INDICATORS AND REAGENTS; KETONES; KINETICS; MANGANESE; OXIDATION-REDUCTION; PORPHYRINS; QUATERNARY AMMONIUM COMPOUNDS; SOLVENTS;

EID: 33947127135     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2007.01.032     Document Type: Article

References (53)

1. Sheldon R.A., and Kochi J.K. Metal-Catalyzed Oxidation of Organic Compounds (1981), Academic, New York
2. Hudlicky M. Oxidations in Organic Chemistry (1990), ACS, Washington, DC
3. Larock R.C. Comperhensive Organic Transformations (1989), VCH, New York p 604
4. Procter G. In: Ley S.V. (Ed). Comperhensive Organic Synthesis Vol. 7 (1991), Pergamon, Oxford
5. Lee T.V. In: Trost B.M., and Fleming I. (Eds). Comperhensive Organic Synthesis Vol. 2 (1991), Pergamon, Oxford
6. Sheldon R.A., Arends I.W.C.E., and Dijkman A. Catal. Today 57 (2000) 157
7. Ley S.V., Norman J., Griffith W.P., and Marsden S.P. Synthesis (1994) 639
8. Murahashi S.-I., Naota T., Oda Y., and Hirai N. Synlett (1995) 733
9. Krohn K., Vinke I., and Adam H. J. Org. Chem. 61 (1996) 1467 and references therein
10. Schultz M.J., and Sigman M.S. Tetrahedron 62 (2006) 8227
11. Stack T.D.P. Dalton Trans. (2003) 1881
12. Jazdzewski B.A., and Tolman W.B. Coord. Chem. Rev. 200-202 (2000) 633
13. Itoh S., Taki M., and Fukuzumi S. Coord. Chem. Rev. 198 (2000) 3
14. Pratt R.C., and Stack T.D.P. J. Am. Chem. Soc. 125 (2003) 8716
15. Thomas F., Gellon G., Gautier-Luneau I., Saint-Aman E., and Pierre J.-L. Angew. Chem., Int. Ed. 41 (2002) 3047
16. Chaudhuri P., Hess M., Muller J., Hildenbrand K., Bill E., Weyhermuller T., and Wieghardt K. J. Am. Chem. Soc. 121 (1999) 9599
17. Itoh S., Taki M., Takayama S., Nagatomo S., Kitagawa T., Sakurada N., Arakawa R., and Fukuzumi S. Angew. Chem., Int. Ed 38 (1999) 2774
18. Vaz A.D.N., and Coon M.J. Biochemistry 331 (1994) 6442
19. McMurry T.J., and Groves J.T. In: Ortiz de Montellano P.R. (Ed). Cytochrome P-450: Mechanism and Biochemistry (1986), Plenum, New York and London Chapter 1
20. Tabushi I. Coord. Chem. Rev. 861 (1988) 1
21. Meunier B. Chem. Rev. 92 (1992) 1411
22. Mansuy D. Coord. Chem. Rev. 125 (1993) 129
23. Groves, J.; Shalyaev, T. K.; Lee, J. In The Porphyrin Handbook; Kadish, K. M., Smith, K. M., Guilard, R., Eds.; Academic: San Diego, 1999; Chapter 27, p 17.
24. Mansuy, D.; Battioni, P. In The Porphyrin Handbook, Kadish, K. M., Smith, K. M., Guilard, R., Eds.; Academic: San Diego, 2000, Vol. 4, Chapter 26, p 1.
25. Tabushi I., and Koga N. Tetrahedron Lett. (1979) 3681
26. Labat G., and Meunier B. J. Org. Chem. 54 (1989) 5008
27. Wietzerbin K., Meunier B., and Bernadou J. Chem. Commun. (1997) 2321
28. Baciocchi E., and Belvedere S. Tetrahedron Lett. 39 (1998) 4711
29. Campestrini S., and Cagnina A. J. Mol. Catal. A: Chem. 150 (1999) 77
30. Moghadam M., Tangestaninejad S., Mirkhani V., Mohammadpoor-Baltork I., and Kargar H. Bioorg. Med. Chem. 13 (2005) 2901
31. Naik R., Joshi P., and Deshpande R.K. J. Mol. Catal. A: Chem. 238 (2005) 46
32. Han J., Yoo S.-K., Seo J.S., Hong S.J., Kim S.K., and Kim C. Dalton Trans. (2005) 402
33. Oh N.Y., Suh Y., Park M.J., Seo M.S., Kim J., and Nam W. Angew. Chem., Int. Ed. 44 (2005) 4235
34. Huang J.-Y., Li S.-J., and Wang Y.-G.. Tetrahedron Lett. 47 (2006) 5637
35. Mohajer D., and Rezaeifard A. Tetrahedron Lett. 43 (2002) 1881
36. Iranpoor N., Mohajer D., and Rezaeifard A.-R. Tetrahedron Lett. 45 (2004) 3811
37. Mohajer D., Karimpour G., and Bagherzadeh M. New J. Chem. 28 (2004) 740
38. Adam W., Stegmann V.R., and Saha-Moller C.R. J. Am. Chem. Soc. 121 (1999) 1879
39. Baumstark L., Beeson M., and Vasquez P.C. Tetrahedron Lett. 30 (1989) 5567
40. Webb K.S., and Ruszkay S.J. Tetrahedron 54 (1998) 401
41. Traylor P.S., Dolphin D., and Traylor T.G. J. Chem. Soc., Chem. Commun. (1984) 279
42. Banfi S., Montanari F., and Quici S. J. Org. Chem. 54 (1989) 1850
43. Tralor T.G., Kim C., Richards J.L., Xu F., and Perrin C.L. J. Am. Chem. Soc. 117 (1995) 3468
44. Dolphin D., Traylor T.G., and Xie L.Y. Acc. Chem. Res 30 (1997) 251
45. Goh Y.M., and Nam W. Inorg. Chem. 38 (1999) 914
46. Nam W., Oh S.-Y., Sun Y.J., Kim J., Woo S.K., and Shin W. J. Org. Chem. 68 (2003) 7903
47. Trost B.M., and Braslau R. J. Org. Chem. 53 (1988) 532
48. Campestrini S., and Meunier B. Inorg. Chem. 31 (1992) 1999
49. 5 should be considered as a potential explosive
50. Adler A.D., Longo F.R., Finarelli J.D., Goldmacher J., Assour J., and Korsakoff L. J. Org. Chem. 3 (1967) 476
51. Bettelheim A., White B.A., Raybuck S.A., and Murray R.W. Inorg. Chem. 26 (1987) 1009
52. Hoffmann P., Robert A., and Meunier B. Bull. Soc. Chim. Fr. 129 (1992) 85
53. Adler A.D., Longo F.R., Kampas F., and Kim J. J. Inorg. Nucl. Chem. 32 (1970) 2443