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

被引:29
作者
Fauq, AH [1 ]
Hong, F [1 ]
Cusack, B [1 ]
Tyler, BM [1 ]
Ping-Pang, Y [1 ]
Richelson, E [1 ]
机构
[1] Mayo Clin Jacksonville, Jacksonville, FL 32224 USA
基金
美国国家卫生研究院;
关键词
D O I
10.1016/S0957-4166(98)00445-5
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
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 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. (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:4127 / 4134
页数:8
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