Preparation of 'side-chain-to-side-chain' cyclic peptides by Allyl and Alloc strategy: Potential for library synthesis

P. Grieco, P. M. Gitu, V. J. Hruby

Research output: Contribution to journalArticle

76 Scopus citations

Abstract

Automated and manual deprotection methods for allyl/allyloxycarbonyl (Allyl/Alloc) were evaluated for the preparation of side-chain-to-side-chain cyclic peptides. Using a standard Allyl/Alloc deprotection method, a small library of cyclic peptides with lactam bridges (with seven amino acids) was prepared on an automatic peptide synthesizer. We demonstrate that the Guibé method for removing Allyl/Alloc protecting groups under specific neutral conditions [Pd(PPh3)4/PhSiH3)/DCM] can be a useful, efficient and reliable method for preparing long cyclic peptides on a resin. We have also manually synthesized a cyclic glucagon analogue containing 24 amino acid residues. These results demonstrated that properly controlled palladium-mediated deprotection of Allyl/Alloc protecting groups can be used to prepare cyclic peptides on the resin using an automated peptide synthesizer and cyclic peptides with a long chain.

Original languageEnglish (US)
Pages (from-to)250-256
Number of pages7
JournalJournal of Peptide Research
Volume57
Issue number3
DOIs
StatePublished - Apr 2 2001

Keywords

  • Allyl/Alloc strategy
  • Automated synthesis
  • Cyclic peptides
  • Side-chain-to-side-chain cyclization
  • Solid-phase synthesis

ASJC Scopus subject areas

  • Biochemistry
  • Endocrinology

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