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research article

Manganese Transfer Hydrogenases Based on the Biotin-Streptavidin Technology

Wang, Weijin  
•
Tachibana, Ryo
•
Zou, Zhi
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October 23, 2023
Angewandte Chemie International Edition

Artificial (transfer) hydrogenases have been developed for organic synthesis, but they rely on precious metals. Native hydrogenases use Earth-abundant metals, but these cannot be applied for organic synthesis due, in part, to their substrate specificity. Herein, we report the design and development of manganese transfer hydrogenases based on the biotin-streptavidin technology. By incorporating bio-mimetic Mn(I) complexes into the binding cavity of streptavidin, and through chemo-genetic optimization, we have obtained artificial enzymes that hydrogenate ketones with nearly quantitative yield and up to 98 % enantiomeric excess (ee). These enzymes exhibit broad substrate scope and high functional-group tolerance. According to QM/MM calculations and X-ray crystallography, the S112Y mutation, combined with the appropriate chemical structure of the Mn cofactor plays a critical role in the reactivity and enantioselectivity of the artificial metalloenzyme (ArMs). Our work highlights the potential of ArMs incorporating base-meal cofactors for enantioselective organic synthesis.|Efficient Mn artificial transfer hydrogenases (ATHases) were developed using the biotin-streptavidin technology, which exhibits high activity and enantioselectivity for the transfer hydrogenation of a wide range of aryl ketones. The S112Y-K121 M double mutation and the appropriate chemical structure of the Mn cofactor play critical roles in the reactivity and enantioselectivity of the enzymes.image

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Type
research article
DOI
10.1002/anie.202311896
Web of Science ID

WOS:001086226000077

Author(s)
Wang, Weijin  
Tachibana, Ryo
Zou, Zhi
Chen, Dongping
Zhang, Xiang
Lau, Kelvin  orcid-logo
Pojer, Florence  
Ward, Thomas R.
Hu, Xile  
Date Issued

2023-10-23

Publisher

Wiley-VCH Verlag GmbH

Published in
Angewandte Chemie International Edition
Volume

62

Issue

43

Article Number

e202311896

Subjects

Physical Sciences

•

Biocatalysis

•

Hydrogenases

•

Hydrogenation

•

Manganese

•

Metalloenzyme

Editorial or Peer reviewed

REVIEWED

Written at

EPFL

EPFL units
LSCI  
FunderGrant Number

Swiss National Science Foundation

200020_212062

NCCR Catalysis

180544

Naito Foundation

Available on Infoscience
February 16, 2024
Use this identifier to reference this record
https://infoscience.epfl.ch/handle/20.500.14299/203890
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