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Appl. Environ. Microbiol., Dec 1996, 4388-4394, Vol 62, No. 12
Copyright © 1996, American Society for Microbiology

Initial reactions in the oxidation of 1,2-dihydronaphthalene by Sphingomonas yanoikuyae strains

SL Eaton, SM Resnick and DT Gibson
Department of Microbiology, College of Medicine, University of Iowa, Iowa City 52242, USA.

The substrate oxidation profiles of Sphingomonas yanoikuyae B1 biphenyl- 2,3-dioxygenase and cis-biphenyl dihydrodiol dehydrogenase activities were examined with 1,2-dihydronaphthalene and various cis-diols as substrates. m-Xylene-induced cells of strain B1 oxidized 1,2- dihydronaphthalene to (-)-(1R,2S)-cis-1,2-dihydroxy-1,2-3,4- tetrahydronaphthalene as the major product (73% relative yield). Small amounts of (+)-(R)-2-hydroxy-1,2-dihydronaphthalene (15%), naphthalene (6%), and alpha-tetralone (6%) were also formed. Strain B8/36, which lacks an active cis-biphenyl dihydrodiol dehydrogenase, formed (+)- (1R,2S)-cis-1,2-dihydroxy-1,2-dihydronaphthalene (51%), in addition to (-)-(1R,2S)-cis-1,2-dihydroxy-1,2,3,4-tetrahydronaphthalene (44%) and (+)-(R)-2-hydroxy-1,2-dihydronaphthalene (5%). The cis-biphenyl dihydrodiol dehydrogenase of strain B1 oxidized both enantiomers of cis- 1,2-dihydroxy-1,2-dihydronaphthalene, but only the (+)-(1S,2R)- enantiomers of cis-1,2-dihydroxy-1,2,3,4-tetrahydronaphthalene and cis- 1,2-dihydroxy-3-phenylcyclohexa-3,5-diene. The results show that biphenyl dioxygenase expressed by S. yanoikuyae catalyzes dioxygenation, monooxygenation, and desaturation reactions with 1,2- dihydronaphthalene as the substrate, and cis-biphenyl dihydrodiol dehydrogenase catalyzes the enantioselective dehydrogenation of (+)- (1S,2R)-cis-1,2-dihydroxy-1,2,3,4-tetrahydronaphthalene and (+)-(1S,2R)- cis-1,2-dihydroxy-3-phenylcyclohexa-3,5-diene.

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