Mechanistic studies of amide bond scission during acidolytic deprotection of Pip containing peptide.

C. Rubini, A. Osler, A. Calderan, Andrea Guiotto, P. Ruzza

Research output: Contribution to journalArticle

6 Citations (Scopus)

Abstract

Unusual TFA catalyzed cleavage reaction is reported for peptide containing pipecolic acid residues. Although the use of TFA under standard cleavage conditions is sufficiently mild to prevent degradation of the desired products. the amide bond between consecutive pipecolic acid residues is unexpectedly hydrolyzed by standard TFA treatment. The hydrolysis is proposed to proceed via an oxazolinium ion intermediate, This mechanism is supported by H/D exchange as observed by ESI-MS and NMR experiments.
Original languageEnglish
Pages (from-to)989-997
Number of pages9
JournalJournal of peptide science
Volume14(8)
Issue number8
DOIs
Publication statusPublished - Aug 2008

ASJC Scopus subject areas

  • Biochemistry, Genetics and Molecular Biology(all)
  • Biochemistry
  • Analytical Chemistry

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