Introduction of α,α-disubstituted α-amino acids and tethered side chain on peptides are effective methods for increasing helical stability of oligopeptides. From this point of view, we designed four- or five-membered ring carbocyclic α,α-disubstituted α-amino acids possessing tethered allyl group on the carbocycle. The carbocyclic α,α-disubstituted α-amino acids were successfully synthesized from 1,3-dichloro-2-propanol or L-malic acid and were introduced to L-leucine sequence. Ring closing metathesis of allyl-tethered peptides using Grubbs catalyst gave exclusively <i>E</i>-alkene. Conformational studies of peptides were also examined based on CD spectra and X-ray crystallographic analyses.

Synthesis and conformational analyses of stapled peptides derived from allyl-tethered carbocyclic α,α-disubstituted α-amino acids

254th National Meeting (2017)

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