Tandem enzyme-catalysed oxidations of alkyl phenyl sulfides and alkyl benzenes: enantiocomplementary routes to chiral phenols.
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.
Boyd
Derek R
DR
School of Chemistry, Queen's University of Belfast, Belfast, UK BT9 5AG. dr.boyd@qub.ac.uk
Sharma
Narain D
ND
Ljubez
Vera
V
Byrne
Breige E
BE
Shepherd
Steven D
SD
Allen
Christopher C R
CC
Kulakov
Leonid A
LA
Larkin
Michael J
MJ
Dalton
Howard
H
D001554:Benzene / Q000737:chemistry / Q000378:metabolism*; D002384:Catalysis; D002396:Catechols / Q000737:chemistry* / Q000378:metabolism*; D007536:Isomerism; D010084:Oxidation-Reduction; D010088:Oxidoreductases / Q000378:metabolism*; D010105:Oxygenases / Q000378:metabolism*; D013440:Sulfides / Q000737:chemistry / Q000378:metabolism*
D002396:Catechols; D013440:Sulfides; D010088:Oxidoreductases; D010105:Oxygenases; D001554:Benzene