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P450-catalyzed asymmetric cyclopropanation of electron-deficient olefins under aerobic conditions.

ABSTRACT: A variant of P450 from Bacillus megaterium five mutations away from wild type is a highly active catalyst for cyclopropanation of a variety of acrylamide and acrylate olefins with ethyl diazoacetate (EDA). The very high rate of reaction enabled by histidine ligation allowed the reaction to be conducted under aerobic conditions. The promiscuity of this catalyst for a variety of substrates containing amides has enabled synthesis of a small library of precursors to levomilnacipran derivatives.

SUBMITTER: Renata H

PROVIDER: S-EPMC4159215 | biostudies-literature | 2014 Oct

REPOSITORIES: biostudies-literature

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P450-catalyzed asymmetric cyclopropanation of electron-deficient olefins under aerobic conditions.

Renata Hans H Wang Z Jane ZJ Kitto Rebekah Z RZ Arnold Frances H FH

Catalysis science & technology 20141001 10

A variant of P450 from Bacillus megaterium five mutations away from wild type is a highly active catalyst for cyclopropanation of a variety of acrylamide and acrylate olefins with ethyl diazoacetate (EDA). The very high rate of reaction enabled by histidine ligation allowed the reaction to be conducted under aerobic conditions. The promiscuity of this catalyst for a variety of substrates containing amides has enabled synthesis of a small library of precursors to levomilnacipran derivative ...[more]

PMID: 25221671

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