Jump to main content
Jump to site search

Issue 4, 2016
Previous Article Next Article

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

Author affiliations

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.

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

Back to tab navigation

Supplementary files

Publication details

The article was received on 13 May 2015, accepted on 15 Sep 2015 and first published on 15 Sep 2015


Article type: Paper
DOI: 10.1039/C5GC01017A
Author version
available:
Download author version (PDF)
Green Chem., 2016,18, 1089-1095

  •   Request permissions

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

    H. Jang, K. Singha, H. Kim, Y. Kwon and J. Park, Green Chem., 2016, 18, 1089
    DOI: 10.1039/C5GC01017A

Search articles by author

Spotlight

Advertisements