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

Eaton, S.; Resnick, Sol M.; Gibson, David T.

doi:10.1128/aem.62.12.4388-4394.1996

Cited by 20 publications

(3 citation statements)

References 36 publications

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“…With respect to enantioselective transformation of cis-1,2indandiol, CDD closely resembles the cis-dihydrodiol dehydrogenase of P. putida NCIMB 8859 (1) but differs from the cis-glycol dehydrogenase of P. putida 421-5. P. putida NCIMB 8859 enantioselectively oxidizes the (Ϫ)-cis-(1R,2S)-enantiomer (1), whereas the cis-biphenyl dihydrodiol dehydrogenase of S. yanoikuyae B1 only oxidizes the (ϩ)-cis-(1S,2R) enantiomer (6).…”

Section: Discussionmentioning

confidence: 99%

“…During the next step in the degradation of aromatic compounds, the cisdihydrodiols are dehydrogenated to catechols by cis-dihydrodiol dehydrogenases. Generally, cis-dihydrodiol dehydrogenases are also broad-substrate enzymes, and most dehydrogenases are able to transform several cis-dihydrodiol isomers (1,6,12,13,18). However, all studies that investigated the stereochemistry of cis-dihydrodiol oxidation, with the exception of one study (16), report that cis-dihydrodiol dehydrogenases catalyze stereoselective transformations.…”

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confidence: 99%

“…The same strain preferentially transforms monosubstituted cisbenzene dihydrodiols with an S configuration at the C atom in meta position with respect to the substituent. The cis-biphenyl dihydrodiol dehydrogenase from Sphingomonas yanoikuyae B1 oxidizes 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-3phenylcyclohexa-3,5-diene (6). The cis-glycol dehydrogenase of P. putida 421-5 (ATCC 55687) enantioselectively transforms cis-(1R,2S)-indandiol (5).…”

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cis -Chlorobenzene Dihydrodiol Dehydrogenase (TcbB) from Pseudomonas sp. Strain P51, Expressed in Escherichia coli DH5α(pTCB149), Catalyzes Enantioselective Dehydrogenase Reactions

Raschke

Fleischmann

Meer

et al. 1999

Appl Environ Microbiol

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cis-Chlorobenzene dihydrodiol dehydrogenase (CDD) fromPseudomonas sp. strain P51, cloned into Escherichia coli DH5α(pTCB149) was able to oxidizecis-dihydrodihydroxy derivatives (cis-dihydrodiols) of dihydronaphthalene, indene, and fourpara-substituted toluenes to the corresponding catechols. During the incubation of a nonracemic mixture ofcis-1,2-indandiol, only the (+)-cis-(1R,2S) enantiomer was oxidized; the (−)-cis-(S,2R) enantiomer remained unchanged. CDD oxidized both enantiomers ofcis-1,2-dihydroxy-1,2,3,4-tetrahydronaphthalene, but oxidation of the (+)-cis-(1S,2R) enantiomer was delayed until the (−)-cis-(1R,2S) enantiomer was completely depleted. When incubated with nonracemic mixtures ofpara-substituted cis-toluene dihydrodiols, CDD always oxidized the major enantiomer at a higher rate than the minor enantiomer. When incubated with racemic 1-indanol, CDD enantioselectively transformed the (+)-(1S) enantiomer to 1-indanone. This stereoselective transformation shows that CDD also acted as an alcohol dehydrogenase. Additionally, CDD was able to oxidize (+)-cis-(1R,2S)-dihydroxy-1,2-dihydronaphthalene, (+)-cis-monochlorobiphenyl dihydrodiols, and (+)-cis-toluene dihydrodiol to the corresponding catechols.

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Section: Discussionmentioning

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cis -Chlorobenzene Dihydrodiol Dehydrogenase (TcbB) from Pseudomonas sp. Strain P51, Expressed in Escherichia coli DH5α(pTCB149), Catalyzes Enantioselective Dehydrogenase Reactions

Raschke

Fleischmann

Meer

et al. 1999

Appl Environ Microbiol

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Microbial Arene Oxidations

Johnson¹

2004

Organic Reactions

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The metabolism of organic molecules by living organisms is of fundamental interest to biologists, microbiologists, and biochemists. The primary avenue of metabolism in most living organisms is via oxidative pathways. The aromatic hydrocarbons (arenes) are subject to such oxidative degradation; their mammalian and microbial systems have been extensively studied. It is the capacity of certain microorganisms to convert by oxidation arenes into arene cis ‐dihydrodiols that provide the foundation of this chapter. Arenes are subject to a variety of oxidations, but the expression “microbial arene oxidation” is used for the specific oxidation discussed here. The assignment of dihydrodiol configuration and the use of mutant strains of microorganisms laid the groundwork for the development of arene oxidation as a process useful to organic synthesis. Other advances discussed in this chapter led to the development of microbial arene oxidations that are suitable for organic synthesis. Attractive features include: the process is one of a very few that disrupts the aromatic system of arenes; the array of functional groups generated in the dihydrodiol products is useful; the process is highly enantioselective, affording pure enantiomerically pure products in most cases. For this chapter, the literature has been reviewed through 2001.

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Sphingomonas

Yabuuchi¹,

Kosako²

2015

Bergey's Manual of Systematics of Archaea and Bacteria

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Sphin.go.mo' nas . Gr. gen. n. sphingos of sphinx; Gr. n. monad unit, monad; M.L. fem. n. Sphingomonas a sphingosine‐containing monad. Proteobacteria / Alphaproteobacteria / Sphingomonadales / Sphingomonadaceae / Sphingomonas Straight or slightly curved rods or ovoid cells 0 . 2–1 . 4 × 0 . 5–4 . 0 μ m . Gram negative. Asporogenous. Reproduction in most species is by binary fission; budding or asymmetric division as visualized by electron microscopy occurs in two species. Motile or nonmotile. A rosette‐like aggregation caused by polar fimbriae occurs in some species. Aerobic , having a strictly respiratory type of metabolism with oxygen as the terminal electron acceptor. Anaerobic nitrate respiration does not occur. Esculin is hydrolyzed. Two species with bacteriochlorophyll a are facultative photoorganotrophs . Colony color varies from orange or yellow to white to nonpigmented. Catalase positive. Oxidase positive or negative. Glucuronosyl ‐( 1 → 1 )‐ ceramide ( SGL‐1 ), galacturonosyl ‐β( 1 → 1 )‐ ceramide ( in several species ), and 2‐hydroxymyristic acid occur , but not 3‐hydroxy fatty acids (Table BXII.α83, Figs.BXII.α85, BXII.α86, and BXII.α87). The lipopolysaccharide (LPS) of the cell wall is replaced by sphingolipids (Figs. BXII.α88 and BXII.α89). C 18:1 ω9c and C 18:1 ω7c are the major nonpolar fatty acids and 2‐hydroxymyristic acid is the major 2‐hydroxy acid (Table BXII.α84). Some species are opportunistic pathogens, causing meningitis, septicemia, peritonitis, and neonatal infections in intensive care units. Pathogenicity toward animals is not known. Free living in natural and man‐made environments. The mol % G + C of the DNA is : 59–68. Type species : Sphingomonas paucimobilis (Holmes, Owen, Evans, MaInick and Wilcox 1977a) Yabuuchi, Yano, Oyaizu, Hashimoto, Ezaki and Yamamoto 1990b, 321 (Effective publication: Yabuuchi, Yano, Oyaizu, Hashimoto, Ezaki and Yamamoto 1990a, 116) ( Pseudomonas paucimobilis Holmes, Owen, Evans, Malnick and Wilcox 1977a, 133.)

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

Cited by 20 publications

References 36 publications

cis -Chlorobenzene Dihydrodiol Dehydrogenase (TcbB) from Pseudomonas sp. Strain P51, Expressed in Escherichia coli DH5α(pTCB149), Catalyzes Enantioselective Dehydrogenase Reactions

cis -Chlorobenzene Dihydrodiol Dehydrogenase (TcbB) from Pseudomonas sp. Strain P51, Expressed in Escherichia coli DH5α(pTCB149), Catalyzes Enantioselective Dehydrogenase Reactions

Microbial Arene Oxidations

Sphingomonas

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