Facile removal of the N-indole-mesitylenesulfonyl protecting group using HF cleavage conditions

Carrie Haskell-Luevano, Lakmal W. Boteju, Victor J. Hruby

Research output: Contribution to journalArticle

7 Scopus citations

Abstract

Nitrogen indole protection of the β-methyltryptophan side-chain residue is important for avoiding undesired side reactions during peptide synthesis. Of great importance is the choice of a side-chain protecting group for orthogonal peptide synthesis and its stability under a variety of chemical conditions required for synthesis of the four isomers of this unusual amino acid. We report here the successful use of the mesitylenesulfonyl (Mts) protecting group for β-methyltryptophan in the synthesis of melanotropin and CCK peptide analogues and the ready cleavage of this protecting group under HF conditions.

Original languageEnglish (US)
Pages (from-to)163-170
Number of pages8
JournalLetters in Peptide Science
Volume1
Issue number4
DOIs
StatePublished - Feb 1 1995

Keywords

  • CCK
  • α-Melanotropin
  • β-Methyltryptophan

ASJC Scopus subject areas

  • Biochemistry

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