Insights into the secondary structures of lactam N-substituted stapled peptides. Issue 20 (13th May 2020)

• Record Type: Journal Article
• Authors: Vasco, Aldrin V.; Moya, Celia G.; Gröger, Stefan; Brandt, Wolfgang; Balbach, Jochen; Pérez, Carlos S.; Wessjohann, Ludger A.; Rivera, Daniel G.
• Is Part Of: Organic & biomolecular chemistry. Volume 18:Issue 20(2020)
• Page Start: 3838
• Page End: 3842
• Publication Date: 2020-05-13
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/d0ob00767f
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : NMR and CD studies together with molecular dynamics simulation reveal new insights into the s- cis /s- trans isomerism and the effect of the lactam bridge N -substituent on the secondary structure of stapled peptides. Abstract : 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.