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Whole-Cell Photoenzymatic Cascades to Synthesize Long-Chain Aliphatic Amines and Esters from Renewable Fatty Acids
- Long-chain aliphatic amines such as (S,Z)-hepta- dec-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 engi- neered 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 octyl- nonanoate 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 g1 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.
Author: | Hee-Jeong Cha, Se-Yeun Hwang, Da-Som Lee, Ravi Kumar Akula, Yong-Uk Kwon, Moritz Voß, Eva Schuiten, Prof. Dr. Uwe T. BornscheuerORCiD, Frank Hollmann, Deok-Kun Oh, Jin-Byung Park |
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URN: | urn:nbn:de:gbv:9-oa-000013-7 |
DOI: | https://doi.org/https://doi.org/10.1002/anie.201915108 |
ISSN: | 1521-3773 |
Parent Title (English): | Angew. Chem. Int. Ed. |
Publisher: | Wiley |
Place of publication: | Hoboken |
Document Type: | Article |
Language: | English |
Year of Completion: | 2020 |
Release Date: | 2022/03/24 |
Tag: | Biocatalysis; fatty acids; hotodecarboxylase; ong-chainaliphaticamines; whole-cellbiocatalysis |
GND Keyword: | Enzym |
Volume: | 59 |
Page Number: | 5 |
First Page: | 7024 |
Last Page: | 7028 |
Faculties: | Mathematisch-Naturwissenschaftliche Fakultät |
DDC class: | 500 Naturwissenschaften und Mathematik / 540 Chemie |
Licence (German): | Urheberrechtlich geschützt |