Asymmetric Biocatalytic Synthesis of 1-Aryltetrahydro-β-carbolines Enabled by "Substrate Walking".
Pictet-Spengler reaction
asymmetric catalysis
biocatalysis
carbolines
enzyme engineering
Journal
Chemistry (Weinheim an der Bergstrasse, Germany)
ISSN: 1521-3765
Titre abrégé: Chemistry
Pays: Germany
ID NLM: 9513783
Informations de publication
Date de publication:
09 Dec 2020
09 Dec 2020
Historique:
received:
04
10
2020
pubmed:
6
10
2020
medline:
24
2
2021
entrez:
5
10
2020
Statut:
ppublish
Résumé
Stereoselective catalysts for the Pictet-Spengler reaction of tryptamines and aldehydes may allow a simple and fast approach to chiral 1-substituted tetrahydro-β-carbolines. Although biocatalysts have previously been employed for the Pictet-Spengler reaction, not a single one accepts benzaldehyde and its substituted derivatives. To address this challenge, a combination of substrate walking and transfer of beneficial mutations between different wild-type backbones was used to develop a strictosidine synthase from Rauvolfia serpentina (RsSTR) into a suitable enzyme for the asymmetric Pictet-Spengler condensation of tryptamine and benzaldehyde derivatives. The double variant RsSTR V176L/V208A accepted various ortho-, meta- and para-substituted benzaldehydes and produced the corresponding chiral 1-aryl-tetrahydro-β-carbolines with up to 99 % enantiomeric excess.
Identifiants
pubmed: 33017078
doi: 10.1002/chem.202004449
pmc: PMC7756766
doi:
Substances chimiques
Carbolines
0
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
16281-16285Subventions
Organisme : F. Hoffmann-La Roche
Informations de copyright
© 2020 The Authors. Published by Wiley-VCH GmbH.
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