Structure, stereochemistry and synthesis of enantiopure cyclohexenone cis-diol bacterial metabolites derived from phenols

Derek R. Boyd; Narain D. Sharma; John F. Malone; Peter M. A. McIntyre; Paul J. Stevenson; Christopher C. R. Allen; Marcin Kwit; Jacek Gawronski

doi:10.1039/C2OB25079A

Structure, stereochemistry and synthesis of enantiopure cyclohexenone cis-diol bacterial metabolites derived from phenols

Derek R. Boyd
, Narain D. Sharma
, John F. Malone
, Peter M. A. McIntyre
, Paul J. Stevenson
, Christopher C. R. Allen
, Marcin Kwit
, Jacek Gawronski

Research output: Contribution to journal › Article › peer-review

10 Citations (Scopus)

Abstract

Biotransformation of 3-substituted and 2,5-disubstituted phenols, using whole cells of P. putida UV4, yielded cyclohexenone cis-diols as single enantiomers; their structures and absolute configurations have been determined by NMR and ECD spectroscopy, X-ray crystallography, and stereochemical correlation involving a four step chemoenzymatic synthesis from the corresponding cis-dihydrodiol metabolites. An active site model has been proposed, to account for the formation of enantiopure cyclohexenone cis-diols with opposite absolute configurations.

Original language	English
Pages (from-to)	6217-6229
Number of pages	13
Journal	Organic and Biomolecular Chemistry
Volume	10
Issue number	30
Early online date	19 Mar 2012
DOIs	https://doi.org/10.1039/C2OB25079A
Publication status	Published - 2012

ASJC Scopus subject areas

Physical and Theoretical Chemistry
Organic Chemistry
Biochemistry

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10.1039/C2OB25079A

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title = "Structure, stereochemistry and synthesis of enantiopure cyclohexenone cis-diol bacterial metabolites derived from phenols",

abstract = "Biotransformation of 3-substituted and 2,5-disubstituted phenols, using whole cells of P. putida UV4, yielded cyclohexenone cis-diols as single enantiomers; their structures and absolute configurations have been determined by NMR and ECD spectroscopy, X-ray crystallography, and stereochemical correlation involving a four step chemoenzymatic synthesis from the corresponding cis-dihydrodiol metabolites. An active site model has been proposed, to account for the formation of enantiopure cyclohexenone cis-diols with opposite absolute configurations. ",

author = "Boyd, \{Derek R.\} and Sharma, \{Narain D.\} and Malone, \{John F.\} and McIntyre, \{Peter M. A.\} and Stevenson, \{Paul J.\} and Allen, \{Christopher C. R.\} and Marcin Kwit and Jacek Gawronski",

year = "2012",

doi = "10.1039/C2OB25079A",

language = "English",

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TY - JOUR

T1 - Structure, stereochemistry and synthesis of enantiopure cyclohexenone cis-diol bacterial metabolites derived from phenols

AU - Boyd, Derek R.

AU - Sharma, Narain D.

AU - Malone, John F.

AU - McIntyre, Peter M. A.

AU - Stevenson, Paul J.

AU - Allen, Christopher C. R.

AU - Kwit, Marcin

AU - Gawronski, Jacek

PY - 2012

Y1 - 2012

N2 - Biotransformation of 3-substituted and 2,5-disubstituted phenols, using whole cells of P. putida UV4, yielded cyclohexenone cis-diols as single enantiomers; their structures and absolute configurations have been determined by NMR and ECD spectroscopy, X-ray crystallography, and stereochemical correlation involving a four step chemoenzymatic synthesis from the corresponding cis-dihydrodiol metabolites. An active site model has been proposed, to account for the formation of enantiopure cyclohexenone cis-diols with opposite absolute configurations.

AB - Biotransformation of 3-substituted and 2,5-disubstituted phenols, using whole cells of P. putida UV4, yielded cyclohexenone cis-diols as single enantiomers; their structures and absolute configurations have been determined by NMR and ECD spectroscopy, X-ray crystallography, and stereochemical correlation involving a four step chemoenzymatic synthesis from the corresponding cis-dihydrodiol metabolites. An active site model has been proposed, to account for the formation of enantiopure cyclohexenone cis-diols with opposite absolute configurations.

U2 - 10.1039/C2OB25079A

DO - 10.1039/C2OB25079A

M3 - Article

SN - 1477-0520

VL - 10

SP - 6217

EP - 6229

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

IS - 30

ER -

Structure, stereochemistry and synthesis of enantiopure cyclohexenone cis-diol bacterial metabolites derived from phenols

Abstract

ASJC Scopus subject areas

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