Biocatalytic desymmetrization of an atropisomer with both an enantioselective oxidase and ketoreductases

Bo Yuan; Abigail Page; Christopher P. Worrall; Franck Escalettes; Simon C. Willies; Joseph J W McDouall; Nicholas J. Turner; Jonathan Clayden

doi:10.1002/anie.201002580

Biocatalytic desymmetrization of an atropisomer with both an enantioselective oxidase and ketoreductases

Bo Yuan, Abigail Page, Christopher P. Worrall, Franck Escalettes, Simon C. Willies, Joseph J W McDouall, Nicholas J. Turner, Jonathan Clayden

School of Chemistry

Research output: Contribution to journal › Article (Academic Journal) › peer-review

98 Citations (Scopus)

Abstract

All roads lead to ⋯ atropisomeric diaryl ethers containing a benzylic hydroxy group and an aldehyde unit. The isomers were synthesized in enantiomerically enriched form by desymmetrizing atroposelective enzymatic oxidation (with a galactose oxidase (GOase) variant) or reduction (with a ketoreductase (KRED); see scheme).

Original language	English
Pages (from-to)	7010-7013
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	49
Issue number	39
Early online date	16 Aug 2010
DOIs	https://doi.org/10.1002/anie.201002580
Publication status	Published - 17 Sept 2010

Research Groups and Themes

Organic & Biological

Keywords

Asymmetric synthesis atropisomerism biocatalysis diaryl ethers enzymes

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title = "Biocatalytic desymmetrization of an atropisomer with both an enantioselective oxidase and ketoreductases",

abstract = "All roads lead to ⋯ atropisomeric diaryl ethers containing a benzylic hydroxy group and an aldehyde unit. The isomers were synthesized in enantiomerically enriched form by desymmetrizing atroposelective enzymatic oxidation (with a galactose oxidase (GOase) variant) or reduction (with a ketoreductase (KRED); see scheme).",

keywords = "Asymmetric synthesis atropisomerism biocatalysis diaryl ethers enzymes",

author = "Bo Yuan and Abigail Page and Worrall, \{Christopher P.\} and Franck Escalettes and Willies, \{Simon C.\} and McDouall, \{Joseph J W\} and Turner, \{Nicholas J.\} and Jonathan Clayden",

year = "2010",

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doi = "10.1002/anie.201002580",

language = "English",

volume = "49",

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T1 - Biocatalytic desymmetrization of an atropisomer with both an enantioselective oxidase and ketoreductases

AU - Yuan, Bo

AU - Page, Abigail

AU - Worrall, Christopher P.

AU - Escalettes, Franck

AU - Willies, Simon C.

AU - McDouall, Joseph J W

AU - Turner, Nicholas J.

AU - Clayden, Jonathan

PY - 2010/9/17

Y1 - 2010/9/17

N2 - All roads lead to ⋯ atropisomeric diaryl ethers containing a benzylic hydroxy group and an aldehyde unit. The isomers were synthesized in enantiomerically enriched form by desymmetrizing atroposelective enzymatic oxidation (with a galactose oxidase (GOase) variant) or reduction (with a ketoreductase (KRED); see scheme).

AB - All roads lead to ⋯ atropisomeric diaryl ethers containing a benzylic hydroxy group and an aldehyde unit. The isomers were synthesized in enantiomerically enriched form by desymmetrizing atroposelective enzymatic oxidation (with a galactose oxidase (GOase) variant) or reduction (with a ketoreductase (KRED); see scheme).

KW - Asymmetric synthesis atropisomerism biocatalysis diaryl ethers enzymes

UR - https://www.scopus.com/pages/publications/77956914045

U2 - 10.1002/anie.201002580

DO - 10.1002/anie.201002580

M3 - Article (Academic Journal)

C2 - 20715245

AN - SCOPUS:77956914045

SN - 1433-7851

VL - 49

SP - 7010

EP - 7013

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 39

ER -

Biocatalytic desymmetrization of an atropisomer with both an enantioselective oxidase and ketoreductases

Abstract

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