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

Authors
Fauq, AH Hong, F Cusack, B Tyler, BM Ping-Pang, Y Richelson, E
Citation
Ah. Fauq et al., Synthesis of (2S)-2-amino-3-(1H-4-indolyl)propanoic acid, a novel tryptophan analog for structural modification of bioactive peptides, TETRAHEDR-A, 9(23), 1998, pp. 4127-4134
Citations number
10
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON-ASYMMETRY
ISSN journal
09574166 → ACNP
Volume
9
Issue
23
Year of publication
1998
Pages
4127 - 4134
Database
ISI
SICI code
0957-4166(199812)9:23<4127:SO(AAN>2.0.ZU;2-U
Abstract
A convenient, multigram synthesis of a never alpha-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 cou ld 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. (C) 1998 Els evier Science Ltd. All rights reserved.