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Chemo-enzymatic synthesis of 11-hydroxyundecanoic acid and 1,11-undecanedioic acid from ricinoleic acid
- Chemo-enzymatic synthesis of 11-hydroxyundecanoic acid and 1,11-undecanedioic acid from ricinoleic acid
- Jang, Hyun-Young; Singha, Kaushik; Kim, Hwan-Hee; Kwon, Yong-Uk; Park, Jin-Byung
- Ewha Authors
- 박진병; 권용억
- SCOPUS Author ID
- 박진병; 권용억
- Issue Date
- Journal Title
- GREEN CHEMISTRY
- GREEN CHEMISTRY vol. 18, no. 4, pp. 1089 - 1095
- ROYAL SOC CHEMISTRY
- SCI; SCIE; SCOPUS
- Document Type
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- A practical chemoenzymatic synthetic method for 11-hydroxyundecanoic acid and 1,11-undecanedioic acid from ricinoleic acid (12-hydroxyoleic acid) was investigated. Biotransformation of ricinoleic acid into the ester (3) via 12-ketooleic acid (2) was driven by recombinant Escherichia coli cells expressing an alcohol dehydrogenase from Micrococcus luteus and the Baeyer-Villiger monooxygenase from Pseudomonas putida KT2440. The carbon-carbon double bond of the ester (3) was chemically reduced, and the ester bond was hydrolyzed to afford n-heptanoic acid (5) and 11-hydroxyundecanoic acid (7), which were converted into other related derivatives. For example, 11-hydroxyundecanoic acid was transformed into 1,11-undecanedioic acid (8) under fairly mild reaction conditions. Whole-cell biotransformation at high cell density (i.e., 20 g dry cells per L) allowed the final ester product concentration and volumetric productivity to reach 53 mM and 6.6 mM h(-1), respectively. The overall molar yield of 1,11-undecanedioic acid from ricinoleic acid was 55% based on the biotransformation and chemical transformation conversion yields of 84% and 65%, respectively.
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