Metal Coordination-directed Hydroxylation of Steroids with a Novel Artificial P-450 Catalyst

Overview

Journal Org Lett

Publisher American Chemical Society

Specialties Biochemistry
Chemistry

Date 2006 Jan 18

PMID 16408887

Citations 7

Authors

Zhenglai Fang

Ronald Breslow

Affiliations

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Abstract

[structure: see text] A novel catalyst has been synthesized in which a manganese-porphyrin unit is linked to two 2,2'-bipyridyl groups and two pentafluorophenyl groups in trans fashion on its four meso positions. Relative to a previous catalyst in which the manganese-porphyrin had four 2,2'-bipyridyl groups, the new catalyst, in the presence of Cu(2+) ions as coordinating linkers, catalyzes the oxidation of a steroid substrate with much better regioselectivity and higher turnover numbers.

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References

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RAO P, Dhanalekshmi S, Littler B, Lindsey J . Rational syntheses of porphyrins bearing up to four different meso substituents. J Org Chem. 2000; 65(22):7323-44. DOI: 10.1021/jo000882k. View

Yang J, Gabriele B, Belvedere S, Huang Y, Breslow R . Catalytic oxidations of steroid substrates by artificial cytochrome p-450 enzymes. J Org Chem. 2002; 67(15):5057-67. DOI: 10.1021/jo020174u. View

Belvedere S, Breslow R . Regioselective oxidation of steroids by a manganese porphyrin carrying metal coordinating groups. Bioorg Chem. 2005; 29(5):321-31. DOI: 10.1006/bioo.2001.1215. View