A CONVENIENT SYNTHESIS OF THE CONFORMATIONALLY CONSTRAINED AMINO-ACID 5,5-DIMETHYLPROLINE

被引:61
作者
MAGAARD, VW
SANCHEZ, RM
BEAN, JW
MOORE, ML
机构
[1] SMITHKLINE BEECHAM PHARMACEUT,DEPT PEPTIDOMIMET RES,KING OF PRUSSIA,PA 19406
[2] SMITHKLINE BEECHAM PHARMACEUT,DEPT PHYS,KING OF PRUSSIA,PA 19406
[3] SMITHKLINE BEECHAM PHARMACEUT,DEPT STRUCT CHEM,KING OF PRUSSIA,PA 19406
关键词
5,5-DIMETHYLPROLINE; SYNTHESIS; CIS PEPTIDE BOND; CONFORMATIONAL CONSTRAINT; CIS-TRANS ISOMERISM;
D O I
10.1016/0040-4039(93)85081-7
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A convenient synthesis of Boc-DL-5,5-dimethylproline methyl ester is described. This conformationally-constrained amino acid may be expected to exist predominantly in the cis peptide bond isomer when incorporated into peptides. The peptide bond in the model peptide Boc-Phe-Me2Pro-OMe is shown to be 90% in the cis isomer.
引用
收藏
页码:381 / 384
页数:4
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