Simultaneous enzyme/Whole-Cell biotransformation of plant oils into C9 carboxylic acids

Eun Yeong Jeon, Joo Hyun Seo, Woo Ri Kang, Min Ji Kim, Jung Hoo Lee, Deok Kun Oh, Jin Byung Park

Research output: Contribution to journalArticlepeer-review

45 Scopus citations

Abstract

Oxyfunctionalization of plant oils such as olive oil and soybean oil into C9 carboxylic acids (e.g., n-nonanoic acid and 9-hydroxynonanoic acid) was investigated. The biotransformation was composed of hydrolysis of plant oils by the Thermomyces lanuginosus lipase (TLL) and C9−C10 double-bond cleavage in unsaturated fatty acids by a serial reaction of a fatty acid double bond-hydratase of Stenotrophomonas maltophilia, an alcohol dehydrogenase of Micrococcus luteus, and a Baeyer−Villiger monooxygenase (BVMO) of Pseudomonas putida KT2440 expressed in Escherichia coli. The newly cloned oleate hydratase allowed one to produce 10-hydroxyoctadecanoic acid and 10-hydroxyoctadec-12-enoic acid at a high rate from oleic acid and linoleic acid, respectively, which are major fatty acid constituents of many plant oils. Furthermore, overexpression of a long chain fatty acid transporter FadL in the recombinant E. coli led to a significant increase of whole-cell biotransformation rates of oleic acid and linoleic acid into the corresponding esters. The resulting esters (the BVMO reaction products) were hydrolyzed in situ by TLL, generating nonanoic acid, non-3-enoic acid, and 9-hydroxynonanoic acid, which can be further oxidized to 1,9-nonanedioic acid. This study demonstrated that industrially relevant C9 carboxylic acids could be produced from olive oil or soybean oil by simultaneous enzyme/whole-cell biocatalysis.

Original languageEnglish
Pages (from-to)7547-7553
Number of pages7
JournalACS Catalysis
Volume6
Issue number11
DOIs
StatePublished - 4 Nov 2016

Keywords

  • 9-hydroxynonanoic acid
  • FadL
  • Oleate hydratase
  • Olive oil
  • Simultaneous enzyme/whole-cell biocatalysis
  • Soybean oil

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