Unique β-Turn Peptoid Structures and Their Application as Asymmetric Catalysts.
beta-turn
foldamers
peptides
peptoids
proline
Journal
Chemistry (Weinheim an der Bergstrasse, Germany)
ISSN: 1521-3765
Titre abrégé: Chemistry
Pays: Germany
ID NLM: 9513783
Informations de publication
Date de publication:
03 Aug 2020
03 Aug 2020
Historique:
received:
05
02
2020
pubmed:
28
3
2020
medline:
27
10
2020
entrez:
28
3
2020
Statut:
ppublish
Résumé
Peptoids, N-substituted glycine oligomers, represent an important class of peptidomimetics that can fold into three-dimensional structures in solution. Most of the folded peptoid structures, however, resemble helices, and this can limit their applications, specifically in asymmetric catalysis. In this work, for the first time, unique examples of pyrrolidine-based β-turn-like peptoids are described and characterized, both in the solid state, by single-crystal X-ray analysis, and in solution, by circular dichroism spectroscopy. Furthermore, their highly efficient and enantioselective catalytic activity for the production of γ-nitro aldehydes by asymmetric Michael reaction in water was demonstrated. The structural properties and DFT-D3 calculations of the new β-turn-like peptoids, as well as catalytic and spectroscopic studies on designed pyrrolidine-based helical peptoids, suggest that the β-turn structure plays a key role in the stereoselectivity of the catalytic reaction.
Identifiants
pubmed: 32216133
doi: 10.1002/chem.202000595
doi:
Substances chimiques
Peptidomimetics
0
Peptoids
0
Glycine
TE7660XO1C
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
9573-9579Subventions
Organisme : Israel Science Foundation
ID : 395/16
Informations de copyright
© 2020 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.
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