Literature DB >> 16669674

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

Marco Landwehr1, Lisa Hochrein, Christopher R Otey, Alex Kasrayan, Jan-E Bäckvall, Frances H Arnold.   

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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Year:  2006        PMID： 16669674      PMCID： PMC2551755          DOI： 10.1021/ja061261x

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  26 in total

Review 1.  Towards large-scale synthetic applications of Baeyer-Villiger monooxygenases.

Authors:  Veronique Alphand; Giacomo Carrea; Roland Wohlgemuth; Roland Furstoss; John M Woodley
Journal:  Trends Biotechnol       Date:  2003-07       Impact factor: 19.536

Review 2.  Mechanism of oxidation reactions catalyzed by cytochrome p450 enzymes.

Authors:  Bernard Meunier; Samuël P de Visser; Sason Shaik
Journal:  Chem Rev       Date:  2004-09       Impact factor: 60.622

3.  Preparation of human metabolites of propranolol using laboratory-evolved bacterial cytochromes P450.

Authors:  Christopher R Otey; Geethani Bandara; James Lalonde; Katsuyuki Takahashi; Frances H Arnold
Journal:  Biotechnol Bioeng       Date:  2006-02-20       Impact factor: 4.530

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

Authors:  Dieter F Münzer; Peter Meinhold; Matthew W Peters; Sabine Feichtenhofer; Herfried Griengl; Frances H Arnold; Anton Glieder; Anna de Raadt
Journal:  Chem Commun (Camb)       Date:  2005-04-06       Impact factor: 6.222

Review 5.  Combined metal catalysis and biocatalysis for an efficient deracemization process.

Authors:  Oscar Pàmies; Jan E Bäckvall
Journal:  Curr Opin Biotechnol       Date:  2003-08       Impact factor: 9.740

6.  Production of R-(-)-mandelic acid from mandelonitrile by Alcaligenes faecalis ATCC 8750.

Authors:  K Yamamoto; K Oishi; I Fujimatsu; K Komatsu
Journal:  Appl Environ Microbiol       Date:  1991-10       Impact factor: 4.792

7.  Fatty acid-specific, regiospecific, and stereospecific hydroxylation by cytochrome P450 (CYP152B1) from Sphingomonas paucimobilis: substrate structure required for alpha-hydroxylation.

Authors:  I Matsunaga; T Sumimoto; A Ueda; E Kusunose; K Ichihara
Journal:  Lipids       Date:  2000-04       Impact factor: 1.880

8.  A P450 BM-3 mutant hydroxylates alkanes, cycloalkanes, arenes and heteroarenes.

Authors:  D Appel; S Lutz-Wahl; P Fischer; U Schwaneberg; R D Schmid
Journal:  J Biotechnol       Date:  2001-06-15       Impact factor: 3.307

9.  Evaluation of alkoxyresorufins as fluorescent substrates for cytochrome P450 BM3 and site-directed mutants.

Authors:  Barbara M A Lussenburg; Lloyd C Babel; Nico P E Vermeulen; Jan N M Commandeur
Journal:  Anal Biochem       Date:  2005-06-01       Impact factor: 3.365

10.  Rational evolution of a medium chain-specific cytochrome P-450 BM-3 variant.

Authors:  Q S Li; U Schwaneberg; M Fischer; J Schmitt; J Pleiss; S Lutz-Wahl; R D Schmid
Journal:  Biochim Biophys Acta       Date:  2001-02-09
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  20 in total

Review 1.  Enzymatic functionalization of carbon-hydrogen bonds.

Authors:  Jared C Lewis; Pedro S Coelho; Frances H Arnold
Journal:  Chem Soc Rev       Date:  2010-11-15       Impact factor: 54.564

Review 2.  Directed evolution drives the next generation of biocatalysts.

Authors:  Nicholas J Turner
Journal:  Nat Chem Biol       Date:  2009-08       Impact factor: 15.040

3.  Role of residue 87 in substrate selectivity and regioselectivity of drug-metabolizing cytochrome P450 CYP102A1 M11.

Authors:  Eduardo Vottero; Vanina Rea; Jeroen Lastdrager; Maarten Honing; Nico P E Vermeulen; Jan N M Commandeur
Journal:  J Biol Inorg Chem       Date:  2011-05-13       Impact factor: 3.358

4.  A Continuing Career in Biocatalysis: Frances H. Arnold.

Authors:  Rudi Fasan; S B Jennifer Kan; Huimin Zhao
Journal:  ACS Catal       Date:  2019-09-17       Impact factor: 13.084

5.  One-bead-one-catalyst approach to aspartic acid-based oxidation catalyst discovery.

Authors:  Phillip A Lichtor; Scott J Miller
Journal:  ACS Comb Sci       Date:  2011-04-06       Impact factor: 3.784

6.  Structural evidence: a single charged residue affects substrate binding in cytochrome P450 BM-3.

Authors:  Jaclyn Catalano; Kianoush Sadre-Bazzaz; Gabriele A Amodeo; Liang Tong; Ann McDermott
Journal:  Biochemistry       Date:  2013-09-16       Impact factor: 3.162

7.  A panel of cytochrome P450 BM3 variants to produce drug metabolites and diversify lead compounds.

Authors:  Andrew M Sawayama; Michael M Y Chen; Palaniappan Kulanthaivel; Ming-Shang Kuo; Horst Hemmerle; Frances H Arnold
Journal:  Chemistry       Date:  2009-11-02       Impact factor: 5.236

8.  Microbial hydroxylation of o-bromophenylacetic acid: synthesis of 4-substituted-2,3-dihydrobenzofurans.

Authors:  Prashant P Deshpande; Venkata B Nanduri; Annie Pullockaran; Hamish Christie; Richard H Mueller; Ramesh N Patel
Journal:  J Ind Microbiol Biotechnol       Date:  2008-05-22       Impact factor: 3.346

Review 9.  Engineering cytochrome P450 biocatalysts for biotechnology, medicine and bioremediation.

Authors:  Santosh Kumar
Journal:  Expert Opin Drug Metab Toxicol       Date:  2010-02       Impact factor: 4.481

10.  Chemo-enzymatic fluorination of unactivated organic compounds.

Authors:  Andrea Rentmeister; Frances H Arnold; Rudi Fasan
Journal:  Nat Chem Biol       Date:  2008-11-16       Impact factor: 15.040
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