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

62 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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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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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

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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

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ER -

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

Abstract

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Keywords

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