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Whole‐Cell Photoenzymatic Cascades to Synthesize Long‐Chain Aliphatic Amines and Esters from Renewable Fatty Acids
Author(s) -
Cha HeeJeong,
Hwang SeYeun,
Lee DaSom,
Kumar Akula Ravi,
Kwon YongUk,
Voß Moritz,
Schuiten Eva,
Bornscheuer Uwe T.,
Hollmann Frank,
Oh DeokKun,
Park JinByung
Publication year - 2020
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201915108
Subject(s) - ricinoleic acid , chemistry , oleic acid , organic chemistry , fatty acid , pseudomonas putida , biocatalysis , amine gas treating , alcohol dehydrogenase , lipase , biochemistry , alcohol , enzyme , ionic liquid , castor oil , catalysis
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.