Insights into the secondary structures of lactam N-substituted stapled peptides

Stapled peptides derived from the Ugi macrocyclization comprise a special class of cyclopeptides with an N-substituted lactam bridge cross-linking two amino acid side chains. Herein we report a comprehensive analysis of the structural factors influencing the secondary structure of these cyclic pepti...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2020-05, Vol.18 (20), p.3838-3842
Main Authors: Vasco, Aldrin V, Moya, Celia G, Gröger, Stefan, Brandt, Wolfgang, Balbach, Jochen, Pérez, Carlos S, Wessjohann, Ludger A, Rivera, Daniel G
Format: Article
Language:English
Subjects:
Amides
Amino acids
Computer applications
Conformation
Crosslinking
NMR
Nuclear magnetic resonance
Peptides
Protein structure
Secondary structure
Substitutes
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Summary:Stapled peptides derived from the Ugi macrocyclization comprise a special class of cyclopeptides with an N-substituted lactam bridge cross-linking two amino acid side chains. Herein we report a comprehensive analysis of the structural factors influencing the secondary structure of these cyclic peptides in solution. Novel insights into the s-cis/s-trans isomerism and the effect of N-functionalization on the conformation are revealed.
ISSN:1477-0520
1477-0539
DOI:10.1039/d0ob00767f