Metal coordination-directed hydroxylation of steroids with a novel artificial P-450 catalyst.
[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.
Fang
Zhenglai
Z
Department of Chemistry, Columbia University, New York, New York 10027, USA.
Breslow
Ronald
R
D015082:2,2'-Dipyridyl / Q000737:chemistry; D001665:Binding Sites; D002384:Catalysis; D003300:Copper / Q000737:chemistry; D003577:Cytochrome P-450 Enzyme System / Q000138:chemical synthesis* / Q000378:metabolism; D006900:Hydroxylation; D008345:Manganese / Q000737:chemistry*; D008665:Metalloporphyrins / Q000737:chemistry*; D015394:Molecular Structure; D010084:Oxidation-Reduction; D013237:Stereoisomerism; D013256:Steroids / Q000737:chemistry*
D008665:Metalloporphyrins; D013256:Steroids; D008345:Manganese; D015082:2,2'-Dipyridyl; D003300:Copper; D003577:Cytochrome P-450 Enzyme System