- Combined Biocatalytic and Chemical Transformations of Oleic Acid to ω-Hydroxynonanoic Acid and α,ω-Nonanedioic Acid
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A practical chemoenzymatic method for the synthesis of 9-hydroxynonanoic acid and 1,9-nonanedioic acid (i.e., azelaic acid) from oleic acid [(9Z)-octadec-9-enoic acid] was investigated. Biotransformation of oleic acid into 9-(nonanoyloxy)nonanoic acid via 10-hydroxyoctadecanoic acid and 10-keto-octadecanoic acid was driven by a C-9 double bond hydratase from Stenotrophomonas maltophilia, an alcohol dehydrogenase from Micrococcus luteus, and a Baeyer–Villiger monooxygenase (BVMO) from Pseudomonas putida KT2440, which was expressed in recombinant Escherichia coli. After production of the ester (i.e., the BVMO reaction product), the compound was chemically hydrolyzed to n-nonanoic acid and 9-hydroxynonanoic acid because n-nonanoic acid is toxic to E. coli. The ester was also converted into 9-hydroxynonanoic acid and the n-nonanoic acid methyl ester, which can be oxygenated into the 9-hydroxynonanoic acid methyl ester by the AlkBGT from P. putida GPo1. Finally, 9-hydroxynonanoic acid was chemically oxidized to azelaic acid with a high yield under fairly mild reaction conditions. For example, whole-cell biotransformation at a high cell density (i.e., 10 g dry cells/L) allowed the final ester product concentration and volumetric productivity to reach 25 mM and 2.8 mM h?1, respectively. The overall molar yield of azelaic acid from oleic acid was 58%, based on the biotransformation and chemical transformation conversion yields of 84% and 68%, respectively. (Figure presented.).
- Koppireddi, Satish,Seo, Joo-Hyun,Jeon, Eun-Yeong,Chowdhury, Partha Sarathi,Jang, Hyun-Young,Park, Jin-Byung,Kwon, Yong-Uk
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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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p. 696 - 703
(2017/12/26)
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