Manganese Transfer Hydrogenases Based on the Biotin-Streptavidin Technology.
Biocatalysis
Hydrogenases
Hydrogenation
Manganese
Metalloenzyme
Journal
Angewandte Chemie (International ed. in English)
ISSN: 1521-3773
Titre abrégé: Angew Chem Int Ed Engl
Pays: Germany
ID NLM: 0370543
Informations de publication
Date de publication:
23 10 2023
23 10 2023
Historique:
received:
15
08
2023
medline:
23
10
2023
pubmed:
6
9
2023
entrez:
6
9
2023
Statut:
ppublish
Résumé
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.
Identifiants
pubmed: 37671593
doi: 10.1002/anie.202311896
doi:
Substances chimiques
Biotin
6SO6U10H04
Streptavidin
9013-20-1
Hydrogenase
EC 1.12.7.2
Manganese
42Z2K6ZL8P
Metalloproteins
0
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
e202311896Informations de copyright
© 2023 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH.
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