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

…, B Cusack, BM Tyler, Y Ping-Pang, E Richelson

Index: Fauq, Abdul H.; Hong, Feng; Cusack, Bernadette; Tyler, Beth M.; Ping-Pang, Yuan; Richelson, Elliott Tetrahedron Asymmetry, 1998 , vol. 9, # 23 p. 4127 - 4134

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Citation Number: 29

Abstract

A convenient, multigram synthesis of a novel α-amino acid (2S)-2-amino-3-(1H-4-indolyl) propanoic acid (1a), 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 Schöllkopf chiral auxiliary reagents for chirality induction during a key step.