Literature DB >> 15900339

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

Dieter F Münzer1, Peter Meinhold, Matthew W Peters, Sabine Feichtenhofer, Herfried Griengl, Frances H Arnold, Anton Glieder, Anna de Raadt.   

Abstract

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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Year:  2005        PMID： 15900339     DOI： 10.1039/b501527h

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN： 1359-7345            Impact factor:   6.222


  8 in total

Review 1.  Use of chemical auxiliaries to control p450 enzymes for predictable oxidations at unactivated C-h bonds of substrates.

Authors:  Karine Auclair; Vanja Polic
Journal:  Adv Exp Med Biol       Date:  2015       Impact factor: 2.622

Review 2.  Controlling substrate specificity and product regio- and stereo-selectivities of P450 enzymes without mutagenesis.

Authors:  Vanja Polic; Karine Auclair
Journal:  Bioorg Med Chem       Date:  2014-06-25       Impact factor: 3.641

3.  Stabilization of the Reductase Domain in the Catalytically Self-Sufficient Cytochrome P450BM3 by Consensus-Guided Mutagenesis.

Authors:  Gloria Saab-Rincón; Hanan Alwaseem; Valeria Guzmán-Luna; Leticia Olvera; Rudi Fasan
Journal:  Chembiochem       Date:  2018-02-12       Impact factor: 3.164

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

Authors:  Marco Landwehr; Lisa Hochrein; Christopher R Otey; Alex Kasrayan; Jan-E Bäckvall; Frances H Arnold
Journal:  J Am Chem Soc       Date:  2006-05-10       Impact factor: 15.419

5.  A single active-site mutation of P450BM-3 dramatically enhances substrate binding and rate of product formation.

Authors:  Donovan C Haines; Amita Hegde; Baozhi Chen; Weiqiang Zhao; Muralidhar Bondlela; John M Humphreys; David A Mullin; Diana R Tomchick; Mischa Machius; Julian A Peterson
Journal:  Biochemistry       Date:  2011-09-06       Impact factor: 3.162

6.  Regio- and stereoselective hydroxylation of 10-undecenoic acid with a light-driven P450 BM3 biocatalyst yielding a valuable synthon for natural product synthesis.

Authors:  Mallory Kato; Daniel Nguyen; Melissa Gonzalez; Alejandro Cortez; Sarah E Mullen; Lionel E Cheruzel
Journal:  Bioorg Med Chem       Date:  2014-06-05       Impact factor: 3.641

7.  Oxygenase-catalyzed desymmetrization of N,N-dialkyl-piperidine-4-carboxylic acids.

Authors:  Anna M Rydzik; Ivanhoe K H Leung; Grazyna T Kochan; Michael A McDonough; Timothy D W Claridge; Christopher J Schofield
Journal:  Angew Chem Int Ed Engl       Date:  2014-08-27       Impact factor: 15.336

Review 8.  A Unique P450 Peroxygenase System Facilitated by a Dual-Functional Small Molecule: Concept, Application, and Perspective.

Authors:  Siyu Di; Shengxian Fan; Fengjie Jiang; Zhiqi Cong
Journal:  Antioxidants (Basel)       Date:  2022-03-10
  8 in total

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