Biocatalytic Formal Asymmetric para-Aminoethylation of Unprotected Phenols to Chiral Amines DOI
Jingqi Zhang, Xuan Deng, Xue Han

et al.

ACS Catalysis, Journal Year: 2024, Volume and Issue: 15(1), P. 81 - 90

Published: Dec. 13, 2024

Enantiomerically pure amines are vital for the development of biologically active compounds in medicine and agriculture. While aminoalkylation phenols is well-established creating nitrogen-containing frameworks, regio- stereoselective para-aminoethylation unprotected underexplored. To fill this gap, we propose a one-pot cascade biocatalysis system asymmetric into chiral amines, using simple pyruvate, NH4Cl, D/l-alanine as starting materials. Utilizing modular approach, successfully performed through sequential process vinylation hydroamination, achieving good conversions (51.0–72.0%) >99% ee both enantiomers amines. Additionally, biobased p-hydroxycinnamic acid l-tyrosine their derivatives were converted with moderate to (39.4–87%) integrating decarboxylation/hydroamination deamination-decarboxylation/hydroamination. This marks successful de novo biosynthesis method formal phenols.

Language: Английский

Promiscuous acyltransferases for ester and amide synthesis in aqueous solution DOI Creative Commons

Benjamin Baumert,

Hannes Meinert, Clemens Cziegler

et al.

Catalysis Today, Journal Year: 2024, Volume and Issue: 442, P. 114925 - 114925

Published: July 9, 2024

Hydrolases are well-known for hydrolyzing esters, amides, carbamates, peptides, or acid anhydrides in the presence of water. However, some them also capable catalyzing reverse reaction (condensation) under certain conditions aqueous systems. Hence, these enzymes called promiscuous hydrolases/acyltransferases. This review deals with their discovery, background information on mechanism action, and significant improvements by enzyme engineering to both enhance product formation decrease undesired hydrolysis targeted acyl products. Their applications biocatalysis exemplified synthesis a wide range esters amides systems, including preparative-scale processes combination hydrolases/acyltransferases other cascade reactions utilize alternative feedstocks from renewable resources, example. Complementary, use ATP-dependent amide synthesizing is covered. Together, represent practically useful alternatives well-established chemical reactions, operating solutions that appeal different industries.

Language: Английский

Citations

4
Chemoenzymatic synthesis DOI Creative Commons
Paweł Borowiecki, Sandy Schmidt

Communications Chemistry, Journal Year: 2025, Volume and Issue: 8(1)

Published: March 13, 2025

Communications Chemistry is pleased to introduce a Collection of research works focused on recent developments within the interdisciplinary field chemoenzymatic synthesis. Here, Guest Editors highlight key themes and look towards future this field.

Language: Английский

Citations

0
Recent advances in upcycling lignocellulosic biomass through chemoenzymatic processes DOI
Guang Yang, Xin Li,

Wang Ma

et al.

Current Opinion in Green and Sustainable Chemistry, Journal Year: 2025, Volume and Issue: 53, P. 101017 - 101017

Published: April 1, 2025

Language: Английский

Citations

0
Editorial overview: Chemical biotechnology paving the way for a sustainable future DOI
Tomohisa Hasunuma, Yong‐Su Jin

Current Opinion in Biotechnology, Journal Year: 2024, Volume and Issue: 90, P. 103215 - 103215

Published: Sept. 28, 2024

Language: Английский

Citations

0
Biocatalytic Formal Asymmetric para-Aminoethylation of Unprotected Phenols to Chiral Amines DOI
Jingqi Zhang, Xuan Deng, Xue Han

et al.

ACS Catalysis, Journal Year: 2024, Volume and Issue: 15(1), P. 81 - 90

Published: Dec. 13, 2024

Enantiomerically pure amines are vital for the development of biologically active compounds in medicine and agriculture. While aminoalkylation phenols is well-established creating nitrogen-containing frameworks, regio- stereoselective para-aminoethylation unprotected underexplored. To fill this gap, we propose a one-pot cascade biocatalysis system asymmetric into chiral amines, using simple pyruvate, NH4Cl, D/l-alanine as starting materials. Utilizing modular approach, successfully performed through sequential process vinylation hydroamination, achieving good conversions (51.0–72.0%) >99% ee both enantiomers amines. Additionally, biobased p-hydroxycinnamic acid l-tyrosine their derivatives were converted with moderate to (39.4–87%) integrating decarboxylation/hydroamination deamination-decarboxylation/hydroamination. This marks successful de novo biosynthesis method formal phenols.

Language: Английский

Citations

0