Arene cis‐Diol Dehydrogenase‐Catalysed Regio‐ and Stereoselective Oxidation of Arene‐, Cycloalkane‐ and Cycloalkene‐cis‐diols to Yield Catechols and Chiral α‐Ketols. Issue 8 (18th May 2015)

• Record Type: Journal Article
• Authors: 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.
• Is Part Of: Advanced synthesis & catalysis. Volume 357:Issue 8(2015)
• Page Start: 1881
• Page End: 1894
• Publication Date: 2015-05-18
• Subjects: alkene‐/arene‐cis‐1, 2‐diols -- catechols -- cis‐diol dehydrogenases -- stereoselectivity -- α‐ketols; Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.201500189
• Languages: English
• ISSNs: 1615-4150

Abstract

Abstract: 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. Abstract :