2008
DOI: 10.1002/chem.200701029
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Conformational Preference and Potential Templates ofN‐Methylated Cyclic Pentaalanine Peptides

Abstract: Systematic N-methylation of all peptide bonds in the cyclic pentapeptide cyclo(-D-Ala-Ala(4)-) has been performed yielding 30 different N-methylated derivatives, of which only seven displayed a single conformation on the NMR time scale. The conformation of these differentially N-methylated peptides was recently reported by us (J. Am. Chem. Soc. 2006, 128, 15 164-15 172). Here we present the conformational characterization of nine additional N-methylated peptides from the previous library which are not homogene… Show more

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Cited by 55 publications
(53 citation statements)
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“…They have the potential to introduce cis-amide bonds into peptide sequences and are well suited to induce β-turns 37 . Their incorporation as turn-inducing elements into cyclic peptides has been well documented by Kessler and co-workers 38,39 .…”
Section: Conformational Elements That Help Bring the Ends Togethermentioning
confidence: 95%
“…They have the potential to introduce cis-amide bonds into peptide sequences and are well suited to induce β-turns 37 . Their incorporation as turn-inducing elements into cyclic peptides has been well documented by Kessler and co-workers 38,39 .…”
Section: Conformational Elements That Help Bring the Ends Togethermentioning
confidence: 95%
“…In order to investigate the influence of multiple N-methylation on the conformational behavior of peptides, Chatterjee et al synthesized a library of 30 N-methylated cyclic alanine pentapeptides containing one d-Ala residue and investigated the influence on the peptide structure [126][127][128]. These peptides can be used as scaffolds in the development of pharmacologically active peptides by exchanging alanine for other amino acids while maintaining one d-amino acid and the N-methylation pattern.…”
Section: N-methyl Amino Acids: Novel Interesting Cyclopeptide Buildinmentioning
confidence: 98%
“…3−7 Their modular synthesis, combined with the favorable impact of macrocyclization on metabolic stability and cell permeability, makes cyclic peptides ideal macrocyclic scaffolds for exploring this chemical space. Furthermore, one-bead-onecompound (OBOC), DNA-encoded and DNA-programmed synthesis methodologies allow large (10 5 ) to very large (10 12 ) libraries of cyclic peptides to be generated and screened, 8−10 while structural diversity and complexity can be achieved by permuting backbone elements such as stereochemistry 11 and backbone N-methylation, 12 variables that can be modulated at the monomer level. Although solid phase peptide synthesis (SPPS) has been thoroughly developed since its first implementation over 50 years ago, 13 achieving side chain diversity in peptide libraries requires access to diverse amino acid building blocks, of which relatively few are commercially available.…”
Section: * S Supporting Informationmentioning
confidence: 99%