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Arene cis ‐Diol Dehydrogenase‐Catalysed Regio‐ and Stereoselective Oxidation of Arene‐, Cycloalkane‐ and Cycloalkene‐ cis ‐diols to Yield Catechols and Chiral α‐Ketols
Author(s) -
Boyd Derek R.,
Sharma Narain D.,
Berberian M. Victoria,
Cleij Marcel,
Hardacre Christopher,
Ljubez Vera,
McConville Gareth,
Stevenson Paul J.,
Kulakov Leonid A.,
Allen Christopher C. R.
Publication year - 2015
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201500189
Subject(s) - chemistry , enantiopure drug , regioselectivity , stereoselectivity , diol , cycloalkane , naphthalene , kinetic resolution , stereochemistry , dehydrogenase , organic chemistry , medicinal chemistry , catalysis , enzyme , enantioselective synthesis
Benzene cis ‐ diol dehydrogenase and naphthalene cis ‐diol dehydrogenase enzymes, expressed in Pseudomonas putida wild‐type and Escherichia coli recombinant strains, were used to investigate regioselectivity and stereoselectivity during dehydrogenations of arene, cyclic alkane and cyclic alkene vicinal cis ‐diols. The dehydrogenase‐catalysed production of enantiopure cis ‐diols, α‐ketols and catechols, using benzene cis ‐ diol dehydrogenase and naphthalene cis ‐diol dehydrogenase, involved both kinetic resolution and asymmetric synthesis methods. The chemoenzymatic production and applications of catechol bioproducts in synthesis were investigated.