- Conversion of oleic acid to 10-ketostearic acid by Sphingobacterium sp. strain O22
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The conversion of oleic acid by a bacterium, tentatively identified as Sphingobacterium thalpophilum strain O22, was investigated. The microorganism was isolated as a stable culture from compost that was enriched with soybean oil outdoors and subsequently with oleic acid in the laboratory. Strain O22 converted oleic acid to products identified as 10-ketostearic acid (95% of the total conversion product) and 10-hydroxystearic acid (5%). This is in contrast to S. thalpophilum strain B-14797, which produces solely 10-hydroxystearic acid. Maximal conversion was reached in about 36 h after the addition of oleic acid to the fermentation broth. The yield of 10-ketostearic acid was approximately 75% from 0.26 g of oleic acid in 30 mL fermentation broth at 28 °C and 200 rpm for 48 h. This is the first report on the major production of 10-ketostearic acid by a microorganism in the genus Sphingobacterium.
- Kuo,Lanser,Kaneshiro,Hou
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- Simultaneous Enzyme/Whole-Cell Biotransformation of C18 Ricinoleic Acid into (R)-3-Hydroxynonanoic Acid, 9-Hydroxynonanoic Acid, and 1,9-Nonanedioic Acid
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Regiospecific oxyfunctionalization of renewable long chain fatty acids into industrially relevant C9 carboxylic acids has been investigated. One example was biocatalytic transformation of 10,12-dihydroxyoctadecanoic acid, which was produced from ricinoleic acid ((9Z,12R)-12-hydroxyoctadec-9-enoic acid) by a fatty acid double bond hydratase, into (R)-3-hydroxynonanoic acid, 9-hydroxynonanoic acid, and 1,9-nonanedioic acid with a high conversion yield of ca. 70%. The biotransformation was driven by enzyme/whole-cell biocatalysts, consisting of the esterase of Pseudomonas fluorescens and the recombinant Escherichia coli expressing the secondary alcohol dehydrogenase of Micrococcus luteus, the Baeyer-Villiger monooxygenase of Pseudomonas putida KT2440 and the primary alcohol/aldehyde dehydrogenases of Acinetobacter sp. NCIMB9871. The high conversion yields and the high product formation rates over 20 U/g dry cells with insoluble reactants indicated that various (poly-hydroxy) fatty acids could be converted into multi-functional products via the simultaneous enzyme/whole-cell biotransformations. This study will contribute to the enzyme-based functionalization of hydrophobic substances. (Figure presented.).
- Cha, Hee-Jeong,Seo, Eun-Ji,Song, Ji-Won,Jo, Hye-Jin,Kumar, Akula Ravi,Park, Jin-Byung
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supporting information
p. 696 - 703
(2017/12/26)
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- PROCESS FOR THE SYNTHESIS OF KETONES FROM INTERNAL ALKENES
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The present invention is directed to methods for oxidizing internal olefins to ketones. In various embodiments, each method comprising contacting an organic substrate, having an initial internal olefin, with a mixture of (a) a biscationic palladium salt; and (b) an oxidizing agent; dissolved or dispersed in a solvent system to form a reaction mixture, said solvent system comprising at least one C2-6 carbon nitrile and optionally at least one secondary alkyl amide, said method conducted under conditions sufficient to convert at least 50 mol % of the initial internal olefin to a ketone, said ketone positioned on a carbon of the initial internal olefin. The transformation occurs at room temperature and shows wide substrate scope. Applications to the oxidation of seed oil derivatives and a bioactive natural product are described.
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Page/Page column 0122; 0135; 0149
(2014/07/22)
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- Practical and general palladium-catalyzed synthesis of ketones from internal olefins
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Make it simple! A convenient and general palladium-catalyzed oxidation of internal olefins to ketones is reported. The transformation occurs at room temperature and shows wide substrate scope. Applications to the oxidation of seed-oil derivatives and a bioactive natural product (see scheme) are described, as well as intriguing mechanistic features. Copyright
- Morandi, Bill,Wickens, Zachary K.,Grubbs, Robert H.
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supporting information
p. 2944 - 2948
(2013/04/10)
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- Biotransformation of Oleic Acid to Optically Active γ-Dodecalactone
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We contemplated the formation of γ-dodecalactone through microbial conversion consisting of two steps, the first for oxidizing oleic acid into 10-hydroxystearic acid and the second for the formation of γ-dodecalactone from the hydroxy acid.Microorganisms were screened for production of 10-hydroxystearic acid from oleic acid.A bacterium which could produce the hydroxy acid with a transformation yield of 61.5percent at a concentration of 5percent oleic acid was isolated.The hydroxy acid was found to be biotransformed to γ-dodecalactone by baker's yeast.The enantiomeric composition of the biosynthetic γ-dodecalactone was estimated to be the (R)- configuration and the optical purity of the lactone was estimated to be 87.6percent e.e.The biotransformation yield from oleic acid to γ-dodecalactone was 22.5percent.
- Gocho, Shinobu,Tabogami, Nariyuki,Inagaki, Masao,Kawabata, Choko,Komai, Tuyosi
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p. 1571 - 1572
(2007/10/02)
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