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Stereoselective hydroxylation of an achiral cyclopentanecarboxylic acid derivative using engineered P450s BM-3.

Chemical communications (Cambridge, England) (2005-05-19)
Dieter F Münzer, Peter Meinhold, Matthew W Peters, Sabine Feichtenhofer, Herfried Griengl, Frances H Arnold, Anton Glieder, Anna de Raadt
RÉSUMÉ

Substrate engineered, achiral carboxylic acid derivative was biohydroxylated with various mutants of cytochrome P450 BM-3 to give two out of the four possible diastereoisomers in high de and ee. The BM-3 mutants exhibit up to 9200 total turnovers for hydroxylation of the engineered substrate, which without the protecting group is not transformed by this enzyme.

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Sigma-Aldrich
3-Oxo-1-cyclopentanecarboxylic acid, 97%