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; Deok Kun Oh; Jin Byung Park

doi:10.1002/anie.201915108

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
, Deok Kun Oh
, Jin Byung Park

Research output: Contribution to journal › Article › peer-review

66 Scopus citations

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 language	English
Pages (from-to)	7024-7028
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	59
Issue number	18
DOIs	https://doi.org/10.1002/anie.201915108
State	Published - 27 Apr 2020

Bibliographical note

Publisher Copyright:
© 2020 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

Keywords

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

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10.1002/anie.201915108

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Cha, H. J., Hwang, S. Y., Lee, D. S., Kumar, A. R., Kwon, Y. U., Voß, M., Schuiten, E., Bornscheuer, U. T., Hollmann, F., Oh, D. K., & Park, J. B. (2020). Whole-Cell Photoenzymatic Cascades to Synthesize Long-Chain Aliphatic Amines and Esters from Renewable Fatty Acids. Angewandte Chemie - International Edition, 59(18), 7024-7028. https://doi.org/10.1002/anie.201915108

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

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.",

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doi = "10.1002/anie.201915108",

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AU - Cha, Hee Jeong

AU - Hwang, Se Yeun

AU - Lee, Da Som

AU - Kumar, Akula Ravi

AU - Kwon, Yong Uk

AU - Voß, Moritz

AU - Schuiten, Eva

AU - Bornscheuer, Uwe T.

AU - Hollmann, Frank

AU - Oh, Deok Kun

AU - Park, Jin Byung

PY - 2020/4/27

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N2 - 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.

AB - 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.

KW - Biocatalysis

KW - fatty acids

KW - long-chain aliphatic amines

KW - photodecarboxylase

KW - whole-cell biocatalysis

UR - https://www.scopus.com/pages/publications/85083689682

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JO - Angewandte Chemie - International Edition

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IS - 18

ER -

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

Abstract

Bibliographical note

Keywords

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