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Chemo-enzymatic synthesis of 11-hydroxyundecanoic acid and 1,11-undecanedioic acid from ricinoleic acid

Title
Chemo-enzymatic synthesis of 11-hydroxyundecanoic acid and 1,11-undecanedioic acid from ricinoleic acid
Authors
Jang, Hyun-YoungSingha, KaushikKim, Hwan-HeeKwon, Yong-UkPark, Jin-Byung
Ewha Authors
박진병권용억
SCOPUS Author ID
박진병scopus; 권용억scopus
Issue Date
2016
Journal Title
GREEN CHEMISTRY
ISSN
1463-9262JCR Link1463-9270JCR Link
Citation
vol. 18, no. 4, pp. 1089 - 1095
Publisher
ROYAL SOC CHEMISTRY
Indexed
SCI; SCIE; SCOPUS WOS
Abstract
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.
DOI
10.1039/c5gc01017a
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엘텍공과대학 > 식품공학전공 > Journal papers
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