Regio- and Stereoselectivity of Particulate Methane Monooxygenase from Methylococcus capsulatus (Bath)

作者: Sean J. Elliott , Mei Zhu , Luke Tso , H.-Hoa T. Nguyen , John H.-K. Yip

DOI: 10.1021/JA971049G

关键词: StereoselectivityProton NMRChemistryMethylococcus capsulatusMethane monooxygenaseSubstrate (chemistry)AlkaneEnantiomeric excessStereochemistryHydroxylation

摘要: The regiospecificity and stereoselectivity of alkane hydroxylation alkene epoxidation by the particulate methane monooxygenase from Methylococcus capsulatus (Bath) was evaluated over a range substrates. Oxidation products were identified conventional GC analysis, oxidation determined combination chiral HPLC methods, as well 1H NMR analysis corresponding (R)-2-acetoxy-2-phenylethanoate ester derivatives in case alkanol products. Alkane found to proceed favoring attack at C-2 position all cases, for n-butane n-pentane characterized an enantiomeric excess 46% 80%, respectively, with preference (R)-alcohol noted both Epoxides formed smaller stereoselectivities. Together, regio- results suggest that equilibrium competing substrate binding modes exists. A simple substrate-binding model incorporates p...

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