Synthesis of 'difficult' peptide sequences:: application of a depsipeptide technique to the Jung-Redemann 10- and 26-mers and the amyloid peptide Aβ(1-42)

被引：160
作者：
Carpino, LA [1 ]
Krause, E
Sferdean, CD
Schümann, M
Fabian, H
Bienert, M
Beyermann, M
机构：
[1] Univ Massachusetts, Dept Chem, Amherst, MA 01003 USA
[2] Inst Mol Pharmacol, D-13125 Berlin, Germany
[3] Robert Koch Inst, D-13353 Berlin, Germany
来源：
TETRAHEDRON LETTERS | 2004年 / 45卷 / 40期
基金：
美国国家卫生研究院; 美国国家科学基金会;
关键词：
depsipeptides; O/N shift; difficult sequences; protecting groups; Bsmoc group; amyloid peptide;
D O I：
10.1016/j.tetlet.2004.07.162
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Recently a 26-mer peptide 1 incorporating Ser and Thr was described as a 'difficult' sequence that could not be synthesized by standard methods. If the first Ser residue was used to incorporate a depsipeptide unit, the resulting hybrid was readily assembled. The 26-mer ester was then converted to the native peptide by an OWN acyl shift. The technique may be general for other systems containing appropriate Ser and Thr units and was demonstrated here for the case of the amyloid peptide Abeta(1-42). (C) 2004 Elsevier Ltd. All rights reserved.
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收藏
页码：7519 / 7523
页数：5
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