Synthesis of (2S)-2-amino-3-(1H-4-indolyl)propanoic acid, a novel tryptophan analog for structural modification of bioactive peptides

Abdul H. Fauq, Feng Hong, Bernadette Cusack, Beth M. Tyler, Yuan Ping-Pang, Elliott Richelson

Research output: Contribution to journalArticle

26 Scopus citations

Abstract

A convenient, multigram synthesis of a novel α-amino acid (2S)-2- amino-3-(1H-4-indolyl)propanoic acid (la), is reported. An Fmoc-t-Boc derivative of this novel regioisomer of the natural aromatic amino acid tryptophan could be readily incorporated into bioactive synthetic peptides using standard solid phase synthesis. The synthesis featured the use of Schollkopf chiral auxiliary reagents for chirality induction during a key step.

Original languageEnglish (US)
Pages (from-to)4127-4134
Number of pages8
JournalTetrahedron Asymmetry
Volume9
Issue number23
DOIs
StatePublished - Dec 11 1998

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ASJC Scopus subject areas

  • Catalysis
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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