The synthesis of cyclic peptides

John N. Lambert, Jeffrey P. Mitchell, Kade D. Roberts

Research output: Contribution to journalReview ArticleResearchpeer-review

233 Citations (Scopus)

Abstract

The synthesis of cyclic peptides by chemoselective cyclization reactions was studied. A resin-bound amino acid was reductively alkylated using an appropriate aldehyde and the resulting secondary amine was then acylated to yield an N-alkylated dipeptide. Deprotection was followed by cleavage using toluene-ethanol solvent mixtures under acidic or basic conditions induced cyclization to yield Diketopiperazines (DKPs). It was concluded that the diverse functionality presented by unprotected linear peptides presented a unique challenge to selective intramolecular connections between different points of the peptide chain.

Original languageEnglish
Pages (from-to)471-484
Number of pages14
JournalJournal of the Chemical Society. Perkin Transactions 1
Issue number5
DOIs
Publication statusPublished - 7 Mar 2001
Externally publishedYes

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