N-Fmoc-protected(α-dipeptidoyl)benzotriazoles for efficient solid-phase peptide synthesis by segment condensation

Alan R. Katritzky, Megumi Yoshioka, Tamari Narindoshvili, Alfred Chung, Niveen M. Khashab

Research output: Contribution to journalArticlepeer-review

17 Scopus citations

Abstract

N-Fmoc-protected(α-aminoacyl)benzotriazoles 1a-d readily afford chiral N-Fmoc-protected-α-dipeptides 2a-f (77-89%). Compounds 2a-f are further converted into N-Fmoc-protected(α-dipeptidoyl)benzotriazoles 3a-f (71% average yield). Under mild microwave irradiation, 3a-f are used in solid-phase peptide segment condensation syntheses to give tri-, tetra-, penta-, hexa-, and heptapeptides (20-68%).

Original languageEnglish (US)
Pages (from-to)182-188
Number of pages7
JournalChemical Biology and Drug Design
Volume72
Issue number3
DOIs
StatePublished - Sep 2008
Externally publishedYes

Keywords

  • Fmoc strategy
  • Microwave irradiation
  • N-Fmoc-protected(α-dipeptidoyl) benzotriazoles
  • Segment condensation
  • Solid-phase peptide synthesis

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Medicine

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