Enantioselective Biocascade Catalysis with a Single Multifunctional Enzyme.
Biocatalysis
Cascade Reactions
Enantioselectivity
Enzymes
Organocatalysis
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:
24 10 2022
24 10 2022
Historique:
received:
17
08
2022
pubmed:
1
9
2022
medline:
21
10
2022
entrez:
31
8
2022
Statut:
ppublish
Résumé
Asymmetric catalytic cascade processes offer direct access to complex chiral molecules from simple substrates and in a single step. In biocatalysis, cascades are generally designed by combining multiple enzymes, each catalyzing individual steps of a sequence. Herein, we report a different strategy for biocascades based on a single multifunctional enzyme that can promote multiple stereoselective steps of a domino process by mastering distinct catalytic mechanisms of substrate activation in a sequential way. Specifically, we have used an engineered 4-oxalocrotonate tautomerase (4-OT) enzyme with the ability to form both enamines and iminium ions and combine their mechanisms of catalysis in a complex sequence. This approach allowed us to activate aldehydes and enals toward the synthesis of enantiopure cyclohexene carbaldehydes. The multifunctional 4-OT enzymes could promote both a two-component reaction and a triple cascade characterized by different mechanisms and activation sequences.
Identifiants
pubmed: 36044588
doi: 10.1002/anie.202212176
doi:
Substances chimiques
Multifunctional Enzymes
0
Aldehydes
0
Cyclohexenes
0
Types de publication
Journal Article
Research Support, Non-U.S. Gov't
Langues
eng
Sous-ensembles de citation
IM
Pagination
e202212176Informations de copyright
© 2022 Wiley-VCH GmbH.
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