Tandem enzyme-catalysed oxidations of alkyl phenyl sulfides and alkyl benzenes: enantiocomplementary routes to chiral phenols

Derek R Boyd; Narain D Sharma; Vera Ljubez; Breige E Byrne; Steven D Shepherd; Christopher C R Allen; Leonid A Kulakov; Michael J Larkin; Howard Dalton

doi:10.1039/b205903g

Tandem enzyme-catalysed oxidations of alkyl phenyl sulfides and alkyl benzenes: enantiocomplementary routes to chiral phenols

Chem Commun (Camb). 2002 Sep 7:(17):1914-5. doi: 10.1039/b205903g.

Authors

Derek R Boyd¹, Narain D Sharma, Vera Ljubez, Breige E Byrne, Steven D Shepherd, Christopher C R Allen, Leonid A Kulakov, Michael J Larkin, Howard Dalton

Affiliation

¹ School of Chemistry, Queen's University of Belfast, Belfast, UK BT9 5AG. [email protected]

PMID: 12271672
DOI: 10.1039/b205903g

Abstract

Dioxygenase-catalysed trioxygenation of alkyl phenyl sulfides and alkyl benzenes yields enantiopure cis-dihydrodiol sulfoxides and triols respectively; naphthalene cis-dihydrodiol dehydrogenase-catalysed aromatisation of these diastereoisomers gives enantiopure catechols of either configuration.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Benzene / chemistry
Benzene / metabolism*
Catalysis
Catechols / chemistry*
Catechols / metabolism*
Isomerism
Oxidation-Reduction
Oxidoreductases / metabolism*
Oxygenases / metabolism*
Sulfides / chemistry
Sulfides / metabolism*

Substances

Catechols
Sulfides
Oxidoreductases
Oxygenases
Benzene