UNSPECIFIED. (1996) Dioxygenase-catalysed oxidation of dihydronaphthalenes to yield arene hydrate and cis-dihydro naphthalenediols. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 (1). pp. 67-74. ISSN 0300-922X

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Abstract

Biotransformation of 1,2- and 1,4-dihydronaphthalene substrates, using growing cultures of Pseudomonas putida UV4, resulted in dioxygenase-catalysed benzylic monohydroxylation, cis-tetrahydro diol and cis-dihydro diol formation, trihydroxylation and dehydrogenation; The arene hydrates, (R)-1,2-dihydronaphthalen-1-ol 5 and (R)-1,4-dihydronaphthalen-1-ol 7, were isolated as enantiopure metabolites while 1,2-dihydronaphthalen-2-ol 8 was found in almost racemic form. The structure, enantiopurity and absolute stereochemistry of these arene hydrates of naphthalene were confirmed by chemical synthesis. Deuterium labelling studies, and the use of enantiomerically pure arene hydrates 5 and 7 as substrates, were used to establish the metabolic pathways for the formation of (1R,2S)-1,2-dihydronaphthalene-1,2-diols 2, from both 1,2-dihydronaphthalene 3 and 1,4-dihydronaphthalene 6 substrates.

Item Type:	Journal Article
Subjects:	Q Science > QD Chemistry
Journal or Publication Title:	JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1
Publisher:	ROYAL SOC CHEMISTRY
ISSN:	0300-922X
Official Date:	7 January 1996
Dates:	Date Event 7 January 1996 UNSPECIFIED
Number:	1
Number of Pages:	8
Page Range:	pp. 67-74
Publication Status:	Published
URI:	http://wrap.warwick.ac.uk/id/eprint/19120

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