Enantioselective alpha-hydroxylation of 2-arylacetic acid derivatives and buspirone catalyzed by engineered cytochrome P450 BM-3.

doi:10.1021/JA061261X

Paper

Enantioselective alpha-hydroxylation of 2-arylacetic acid derivatives and buspirone catalyzed by engineered cytochrome P450 BM-3.

Published May 10, 2006 · M. Landwehr, L. Hochrein, Christopher R. Otey

Journal of the American Chemical Society

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139

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Abstract

Here we report that an engineered microbial cytochrome P450 BM-3 (CYP102A subfamily) efficiently catalyzes the alpha-hydroxylation of phenylacetic acid esters. This P450 BM-3 variant also produces the authentic human metabolite of buspirone, R-6-hydroxybuspirone, with 99.5% ee.

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Study Snapshot

Engineered microbial cytochrome P450 BM-3 efficiently catalyzes alpha-hydroxylation of phenylacetic acid esters and produces the authentic human metabolite of buspirone, R-6-hydroxybuspirone, with 99.5% ee.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

Enantioselective alpha-hydroxylation of 2-arylacetic acid derivatives and buspirone catalyzed by engineered cytochrome P450 BM-3.

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References

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Metal-catalyzed cross-coupling reactions offer a powerful tool for organic synthesis, natural product synthesis, and inorganic synthesis, with applications in various fields.

Enzyme Catalysis in Organic Synthesis

Enzyme catalysis plays a crucial role in organic synthesis, with applications ranging from hydrolysis to oxidation, and enzymes playing a crucial role in various industrial processes.

Citations

Indigo production identifies hotspots in cytochrome P450 BM3 for diversifying aromatic hydroxylation.

Indigo production can identify hotspots in cytochrome P450 BM3 that can be recombined to create multiple-variant libraries with high aromatic hydroxylation activity, accelerating enzyme engineering.

Cobalt Catalyzed α-Hydroxylation of Arylacetic Acid Equivalents with Dioxygen.

Cobalt catalysts enable chemo- and regioselective hydroxylation of arylacetic acid equivalents, leading to mandelic acid derivatives under mild conditions and wide synthetic practicality.

Construction of an enzymatic-chemical cascade involving engineered amine dehydrogenases for the synthesis of chiral non-α-amino acids by substrate engineering and enzyme evolution

Substrate engineering and enzyme evolution successfully create an eco-friendly enzymatic-chemical cascade for the synthesis of diverse non--amino acids with distinct substitution patterns.

Choose Your Own Adventure: A Comprehensive Database of Reactions Catalyzed by Cytochrome P450 BM3 Variants

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This study successfully achieved the stereoselective and efficient biosynthesis of chiral methyl mandelates by engineering a cytochrome P450 hydroxylase, resulting in up to 92% isolated yields and >99% efficiency.

A Unique P450 Peroxygenase System Facilitated by a Dual-Functional Small Molecule: Concept, Application, and Perspective

The dual-functional small molecule-facilitated P450 peroxygenase system shows unique activities and selectivity in oxidizing non-native substrates, offering potential for practical applications in various oxidation reactions.