Abstract
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.).
Original language | English |
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Pages (from-to) | 3084-3092 |
Number of pages | 9 |
Journal | Advanced Synthesis and Catalysis |
Volume | 358 |
Issue number | 19 |
DOIs | |
State | Published - 6 Oct 2016 |
Bibliographical note
Funding Information:This study was supported by the R&D Program of MOTIE/KEIT, Republic of Korea [10044604 and 10044647]. J.-H. Seo was partially supported by Ewha Womans University (RP-Grant 2015).
Publisher Copyright:
© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Keywords
- carboxylic acids
- enzyme catalysis
- fatty acids
- oxidation