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Cytochrome P450 Catalyzed Oxidative Hydroxylation of Achiral Organic Compounds with Simultaneous Creation of Two Chirality Centers in a Single CH Activation Step
Author(s) -
Roiban GheorgheDoru,
Agudo Rubén,
Reetz Manfred T.
Publication year - 2014
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201310892
Subject(s) - chemistry , hydroxylation , diastereomer , stereoselectivity , chirality (physics) , oxidative phosphorylation , enantiomer , stereochemistry , catalysis , cyclohexane , cytochrome p450 , biocatalysis , monooxygenase , organic chemistry , enzyme , reaction mechanism , biochemistry , nambu–jona lasinio model , chiral symmetry breaking , physics , quantum mechanics , quark
Regio‐ and stereoselective oxidative hydroxylation of achiral or chiral organic compounds mediated by synthetic reagents, catalysts, or enzymes generally leads to the formation of one new chiral center that appears in the respective enantiomeric or diastereomeric alcohols. By contrast, when subjecting appropriate achiral compounds to this type of CH activation, the simultaneous creation of two chiral centers with a defined relative and absolute configuration may result, provided that control of the regio‐, diastereo‐, and enantioselectivity is ensured. The present study demonstrates that such control is possible by using wild type or mutant forms of the monooxygenase cytochrome P450 BM3 as catalysts in the oxidative hydroxylation of methylcyclohexane and seven other monosubstituted cyclohexane derivatives.