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 Citations (Scopus)

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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Aromatic Amino Acids
Solid-Phase Synthesis Techniques
tryptophan
activity (biology)
Tryptophan
Peptides
peptides
analogs
Amino Acids
acids
amino acids
Acids
Amino acids
synthesis
Chirality
Carboxylic acids
chirality
reagents
solid phases
induction

ASJC Scopus subject areas

  • Inorganic Chemistry
  • Organic Chemistry
  • Materials Chemistry
  • Drug Discovery

Cite this

Synthesis of (2S)-2-amino-3-(1H-4-indolyl)propanoic acid, a novel tryptophan analog for structural modification of bioactive peptides. / Fauq, Abdul H.; Hong, Feng; Cusack, Bernadette; Tyler, Beth M.; Pang, Yuan-Ping; Richelson, Elliott.

In: Tetrahedron Asymmetry, Vol. 9, No. 23, 11.12.1998, p. 4127-4134.

Research output: Contribution to journalArticle

Fauq, Abdul H. ; Hong, Feng ; Cusack, Bernadette ; Tyler, Beth M. ; Pang, Yuan-Ping ; Richelson, Elliott. / Synthesis of (2S)-2-amino-3-(1H-4-indolyl)propanoic acid, a novel tryptophan analog for structural modification of bioactive peptides. In: Tetrahedron Asymmetry. 1998 ; Vol. 9, No. 23. pp. 4127-4134.
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