Eaton S L, Resnick S M, Gibson D T
Department of Microbiology, College of Medicine, University of Iowa, Iowa City 52242, USA.
Appl Environ Microbiol. 1996 Dec;62(12):4388-94. doi: 10.1128/aem.62.12.4388-4394.1996.
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.
以1,2 - 二氢萘和各种顺式二醇为底物，检测了矢野鞘氨醇单胞菌B1的联苯 - 2,3 - 双加氧酶和顺式联苯二氢二醇脱氢酶的底物氧化谱。间二甲苯诱导的B1菌株细胞将1,2 - 二氢萘氧化为(-)-(1R,2S)-顺式 - 1,2 - 二羟基 - 1,2,3,4 - 四氢萘作为主要产物（相对产率73%）。还形成了少量的(+)-(R)-2 - 羟基 - 1,2 - 二氢萘（15%）、萘（6%）和α - 四氢萘酮（6%）。缺乏活性顺式联苯二氢二醇脱氢酶的B8/36菌株，除了形成(-)-(1R,2S)-顺式 - 1,2 - 二羟基 - 1,2,3,4 - 四氢萘（44%）和(+)-(R)-2 - 羟基 - 1,2 - 二氢萘（5%）外，还形成了(+)-(1R,2S)-顺式 - 1,2 - 二羟基 - 1,2 - 二氢萘（51%）。B1菌株的顺式联苯二氢二醇脱氢酶氧化顺式 - 1,2 - 二羟基 - 1,2 - 二氢萘的两种对映体，但只氧化(+)-(1S,2R)-顺式 - 1,2 - 二羟基 - 1,2,3,4 - 四氢萘和顺式 - 1,2 - 二羟基 - 3 - 苯基环己 - 3,5 - 二烯的(+)-(1S,2R)-对映体。结果表明，矢野鞘氨醇单胞菌表达的联苯双加氧酶以1,2 - 二氢萘为底物催化双加氧、单加氧和去饱和反应，顺式联苯二氢二醇脱氢酶催化(+)-(1S,2R)-顺式 - 1,2 - 二羟基 - 1,2,3,4 - 四氢萘和(+)-(1S,2R)-顺式 - 1,2 - 二羟基 - 3 - 苯基环己 - 3,5 - 二烯的对映选择性脱氢。
