Biological Reaction Engineering for the Preparation of C9 Chemicals from Oleic Acid: 9-Aminononanoic Acid, 1,9-Nonanediol, 9-Amino-1-nonanol, and 1,9-Diaminononane

Se Yeun Hwang, Ji Min Woo, Go Eun Choi, Deok Kun Oh, Joo Hyun Seo, Jin Byung Park

Research output: Contribution to journalArticlepeer-review

3 Scopus citations

Abstract

Engineering of native and recombinant enzyme reactions in whole-cell biocatalysis may allow the production of a variety of chemicals. In particular, fine-tuning of the reaction selectivity may enable the preparation of a desired product to a high conversion. Here, we demonstrated that various C9 chemicals such as 9-aminononanoic acid, 1,9-nonanediol, 9-amino-1-nonanol, and 1,9-diaminononane could be produced from renewable C18 oleic acid. As a representative example, activation of six recombinant enzyme reactions (e.g., fatty acid double bond hydratase, long-chain secondary alcohol dehydrogenase, Baeyer-Villiger monooxygenase, lipase, primary alcohol dehydrogenase, and ω-aminotransferases) with repression of one native enzyme reaction (i.e., aldehyde dehydrogenase) in Escherichia coli-based biocatalysis led to the formation of 9-aminononanoic acid with an isolation yield of 54% from oleic acid via 10-hydroxyoctadecanoic acid, 10-keto-octadecanoic acid, 9-(nonanoyloxy)nonanoic acid, 9-hydroxynonanoic acid, and 9-oxo-nonanoic acid. This study will contribute to biosynthesis of not only ω-aminoalkanoic acids but also ω-amino-1-alkanols and α,ω-diaminoalkanes from renewable fatty acids (e.g., oleic acid and ricinoleic acid).

Original languageEnglish
Pages (from-to)4130-4138
Number of pages9
JournalACS Catalysis
Volume14
Issue number6
DOIs
StatePublished - 15 Mar 2024

Bibliographical note

Publisher Copyright:
© 2024 American Chemical Society.

Keywords

  • 1,9-diaminononane
  • 1,9-nonanediol
  • 9-amino-1-nonanol
  • 9-aminononanoic acid
  • whole-cell biocatalysis

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