Ethoxyethylidene protecting group prevents N-overacylation in aminooxy peptide synthesis

被引：31

作者：

Dulery, Vincent

Renaudet, Olivier ^{[1
]}

Dumy, Pascal ^{[1
]}

机构：

[1] Univ Grenoble 1, CNRS, UMR 5250, ICMG FR 2607,Dept Chim Mol, F-38041 Grenoble 9, France

来源：

TETRAHEDRON | 2007年 / 63卷 / 48期

关键词：

D O I：

10.1016/j.tet.2007.09.015

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We report herein an improved synthetic route for the preparation of homogenous aminooxy peptides suitable for oxime ligation. Aminooxyacetic acid (Aoa) was protected with 1-ethoxyethylidene group (Eei) then incorporated either using PyBOP or as N-hydroxysuccinimidyl ester at N-terminal end or at a lysine side chain into model peptides in solution and on solid support. Due to the Eei protecting group, these new reagents prevent the N-overacylation side reaction in comparison with Boc-Aoa derivatives. Subsequent deprotection under mild acidic conditions gave the corresponding pure aminooxylated peptides. (c) 2007 Elsevier Ltd. All rights reserved.

引用

页码：11952 / 11958

页数：7

共 35 条

[1]

Brask J, 2000, J PEPT SCI, V6, P290, DOI 10.1002/1099-1387(200006)6:6<290::AID-PSC257>3.0.CO

[2]

2-L

[3] TOTAL CHEMICAL SYNTHESIS OF A UNIQUE TRANSCRIPTION FACTOR-RELATED PROTEIN - CMYC-MAX [J].