Whole-Cell Photoenzymatic Cascades to Synthesize Long-Chain Aliphatic Amines and Esters from Renewable Fatty Acids

Hee Jeong Cha, Se Yeun Hwang, Da Som Lee, Akula Ravi Kumar, Yong Uk Kwon, Moritz Voß, Eva Schuiten, Uwe T. Bornscheuer, Frank Hollmann, More Authors

Research output: Contribution to journalArticleScientificpeer-review

15 Citations (Scopus)
9 Downloads (Pure)

Abstract

Long-chain aliphatic amines such as (S,Z)-heptadec-9-en-7-amine and 9-aminoheptadecane were synthesized from ricinoleic acid and oleic acid, respectively, by whole-cell cascade reactions using the combination of an alcohol dehydrogenase (ADH) from Micrococcus luteus, an engineered amine transaminase from Vibrio fluvialis (Vf-ATA), and a photoactivated decarboxylase from Chlorella variabilis NC64A (Cv-FAP) in a one-pot process. In addition, long chain aliphatic esters such as 10-(heptanoyloxy)dec-8-ene and octylnonanoate were prepared from ricinoleic acid and oleic acid, respectively, by using the combination of the ADH, a Baeyer–Villiger monooxygenase variant from Pseudomonas putida KT2440, and the Cv-FAP. The target compounds were produced at rates of up to 37 U g−1 dry cells with conversions up to 90 %. Therefore, this study contributes to the preparation of industrially relevant long-chain aliphatic chiral amines and esters from renewable fatty acid resources.

Original languageEnglish
Pages (from-to)7024-7028
JournalAngewandte Chemie - International Edition
Volume59
Issue number18
DOIs
Publication statusPublished - 2020

Keywords

  • Biocatalysis
  • fatty acids
  • long-chain aliphatic amines
  • photodecarboxylase
  • whole-cell biocatalysis

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