Cell-free in vitro reduction of carboxylates to aldehydes: with crude enzyme preparations to a key pharmaceutical building block

Anna Schwarz; Sebastian Hecko; Florian Rudroff; Jeffrey Kohrt; Roger Howard; Margit Winkler

doi:10.1002/biot.202000315

Cell-free in vitro reduction of carboxylates to aldehydes: with crude enzyme preparations to a key pharmaceutical building block

Anna Schwarz
, Sebastian Hecko
, Florian Rudroff
, Jeffrey Kohrt
, Roger Howard
, Margit Winkler^*

^*Korrespondierende/r Autor/-in für diese Arbeit

Publikation: Beitrag in einer Fachzeitschrift › Artikel › Begutachtung

Abstract

The scarcity of practical methods for aldehyde synthesis in chemistry necessitates the development of mild, selective procedures. Carboxylic acid reductases catalyze aldehyde formation from stable carboxylic acid precursors in an aqueous solution.

Carboxylic acid reductases were employed to catalyze aldehyde formation in a cell‐free system with activation energy and reducing equivalents provided through auxiliary proteins for ATP and NADPH recycling. In situ product removal was used to suppress over‐reduction due to background enzyme activities, and an N‐protected 4‐formyl‐piperidine pharma synthon was prepared in 61% isolated yield.

This is the first report of preparative aldehyde synthesis with carboxylic acid reductases employing crude, commercially available enzyme preparations

Originalsprache	englisch
Aufsatznummer	2000315
Fachzeitschrift	Biotechnology Journal
Jahrgang	16
Ausgabenummer	4
Frühes Online-Datum	27 Nov. 2020
DOIs	https://doi.org/10.1002/biot.202000315
Publikationsstatus	Veröffentlicht - Apr. 2021

UN SDGs

Dieser Output leistet einen Beitrag zu folgendem(n) Ziel(en) für nachhaltige Entwicklung

SDG 3 – Gute Gesundheit und Wohlergehen

ASJC Scopus subject areas

Angewandte Mikrobiologie und Biotechnologie
Molekularmedizin

Fields of Expertise

Human- & Biotechnology

Zugriff auf Dokument

10.1002/biot.202000315Lizenz: CC BY-NC 4.0

Andere Dateien und Links

https://www.scopus.com/pages/publications/85099837808

2 Poster
2 Artikel

Multi-enzyme catalysed processes using purified and whole-cell biocatalysts towards a 1,3,4-substituted tetrahydroisoquinoline
Weber, D., de Souza Bastos, L., Winkler, M., Ni, Y., Aliev, A. E., Hailes, H. C. & Rother, D., März 2023, in: RSC Advances . 15, S. 10097-10109
Publikation: Beitrag in einer Fachzeitschrift › Artikel › Begutachtung

Open Access
A cell-free in vitro reduction of carboxylate to aldehyde
Schwarz, A., Strohmeier, G., Eiteljörg, I., Kohrt, J., Howard, R. & Winkler, M., Nov. 2019.
Publikation: Konferenzbeitrag › Poster
A Multi-Enzyme System for the In vitro Reduction of Carboxylic Acids to Aldehydes
Strohmeier, G., Schwarz, A., Eiteljörg, I., Kohrt, J., Howard, R. & Winkler, M., Juli 2019.
Publikation: Konferenzbeitrag › Poster

Dieses zitieren

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keywords = "aldehyde, biocatalysis, carboxylic acid reductase (CAR), in vitro cofactor recycling, pharma synthon",

author = "Anna Schwarz and Sebastian Hecko and Florian Rudroff and Jeffrey Kohrt and Roger Howard and Margit Winkler",

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AU - Howard, Roger

AU - Winkler, Margit

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AB - The scarcity of practical methods for aldehyde synthesis in chemistry necessitates the development of mild, selective procedures. Carboxylic acid reductases catalyze aldehyde formation from stable carboxylic acid precursors in an aqueous solution. Carboxylic acid reductases were employed to catalyze aldehyde formation in a cell‐free system with activation energy and reducing equivalents provided through auxiliary proteins for ATP and NADPH recycling. In situ product removal was used to suppress over‐reduction due to background enzyme activities, and an N‐protected 4‐formyl‐piperidine pharma synthon was prepared in 61% isolated yield. This is the first report of preparative aldehyde synthesis with carboxylic acid reductases employing crude, commercially available enzyme preparations

KW - aldehyde

KW - biocatalysis

KW - carboxylic acid reductase (CAR)

KW - in vitro cofactor recycling

KW - pharma synthon

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VL - 16

JO - Biotechnology Journal

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Cell-free in vitro reduction of carboxylates to aldehydes: with crude enzyme preparations to a key pharmaceutical building block

Abstract

UN SDGs

ASJC Scopus subject areas

Fields of Expertise

Zugriff auf Dokument

Andere Dateien und Links

Fingerprint

Publikationen

Multi-enzyme catalysed processes using purified and whole-cell biocatalysts towards a 1,3,4-substituted tetrahydroisoquinoline

A cell-free in vitro reduction of carboxylate to aldehyde

A Multi-Enzyme System for the In vitro Reduction of Carboxylic Acids to Aldehydes

Dieses zitieren