Thiazolidines to lock cis Xaa-Pro amide bond:: new synthetic approach

被引:6
作者
Chierici, S
Figuet, M
Dettori, A
Dumy, P
机构
[1] Univ Grenoble 1, LEDSS, UMR 5616, F-38041 Grenoble, France
[2] Univ Grenoble 1, FR2607, ICMG, F-38041 Grenoble, France
关键词
2,2-dimethylthiazolidine; Cis proline bond; N-allyloxycarbonyl group; peptide synthesis; tandem deprotection-coupling reaction;
D O I
10.1016/j.crci.2005.02.005
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Thiazolidines, especially the 2,2-dimethylated residue Cys(Psi(Me,Me)pro), are efficient tools to lock Xaa-Pro amide bond to the cis conformation. We investigated herein a new synthetic approach to incorporate these proline mimics instead of the proline into a peptide sequence using N alpha-protected derivatives by a fluorenylmethyl or an allyl carbamate. (c) 2005 Academie des sciences. Published by Elsevier SAS. All rights reserved.
引用
收藏
页码:875 / 880
页数:6
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