Synthesis and 19F spectra of tetra‐L‐alanine analogs containing selectively incorporated 3‐fluoro‐l‐alanine residues

ALOK K. MITRA, IOSIF OSTASHEVSKY, CURTIS F. BREWER

Research output: Contribution to journalArticle

4 Scopus citations

Abstract

The synthesis of analogs of tetra‐l‐alanine containing 3‐fluoro‐l‐alanine selectively incorporated at each position is described. The standard procedures in the literature used to couple l‐alanine peptides together were often found to lead to undesired products, or elimination reactions when corresponding 3‐fluoro‐l‐alanine peptide analogs were used. Several modified procedures have thus been developed for the synthesis of fluorine‐substituted analogs. In addition, the pH‐dependence of 19F n.m.r. spectra of 3‐fluoro‐l‐alanine and the tetrapeptide analogs is presented.

Original languageEnglish (US)
Pages (from-to)495-501
Number of pages7
JournalInternational Journal of Peptide and Protein Research
Volume22
Issue number4
DOIs
StatePublished - Oct 1983

Keywords

  • 19F n.m.r.
  • fluoropeptides
  • peptide synthesis

ASJC Scopus subject areas

  • Biochemistry

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