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; null More Authors

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^*, More Authors

^*Corresponding author for this work

BT/Biocatalysis

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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.

Original language	English
Pages (from-to)	7024-7028
Journal	Angewandte Chemie - International Edition
Volume	59
Issue number	18
DOIs	https://doi.org/10.1002/anie.201915108
Publication status	Published - 2020

Bibliographical note

Green Open Access added to TU Delft Institutional Repository ‘You share, we take care!’ – Taverne project https://www.openaccess.nl/en/you-share-we-take-care Otherwise as indicated in the copyright section: the publisher is the copyright holder of this work and the author uses the Dutch legislation to make this work public.

Keywords

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

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.1002/anie.201915108

anie.201915108taverneFinal published version, 2.49 MB

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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.",

keywords = "Biocatalysis, fatty acids, long-chain aliphatic amines, photodecarboxylase, whole-cell biocatalysis",

author = "Cha, {Hee Jeong} and Hwang, {Se Yeun} and Lee, {Da Som} and Kumar, {Akula Ravi} and Kwon, {Yong Uk} and Moritz Vo{\ss} and Eva Schuiten and Bornscheuer, {Uwe T.} and Frank Hollmann and {More Authors}",

note = "Green Open Access added to TU Delft Institutional Repository {\textquoteleft}You share, we take care!{\textquoteright} – Taverne project https://www.openaccess.nl/en/you-share-we-take-care Otherwise as indicated in the copyright section: the publisher is the copyright holder of this work and the author uses the Dutch legislation to make this work public.",

year = "2020",

doi = "10.1002/anie.201915108",

language = "English",

volume = "59",

pages = "7024--7028",

journal = "Angewandte Chemie - International Edition",

issn = "1433-7851",

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T1 - Whole-Cell Photoenzymatic Cascades to Synthesize Long-Chain Aliphatic Amines and Esters from Renewable Fatty Acids

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 - More Authors, null

N1 - Green Open Access added to TU Delft Institutional Repository ‘You share, we take care!’ – Taverne project https://www.openaccess.nl/en/you-share-we-take-care Otherwise as indicated in the copyright section: the publisher is the copyright holder of this work and the author uses the Dutch legislation to make this work public.

PY - 2020

Y1 - 2020

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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U2 - 10.1002/anie.201915108

DO - 10.1002/anie.201915108

M3 - Article

C2 - 31957098

SN - 1433-7851

VL - 59

SP - 7024

EP - 7028

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 18

ER -

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

Abstract

Bibliographical note

Keywords

UN SDGs

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