Aspartyl methyl ester formation via aspartimide ring opening: a proposed modification of the protocols used in Boc- and Fmoc-based solid-phase peptide synthesis

被引：7

作者：

Kostidis, S ^{[1
]}

Stathopoulos, P ^{[1
]}

Chondrogiannis, NI ^{[1
]}

Sakarellos, C ^{[1
]}

Tsikaris, V ^{[1
]}

机构：

[1] Univ Ioannina, Dept Chem, GR-45110 Ioannina, Greece

来源：

TETRAHEDRON LETTERS | 2003年 / 44卷 / 48期

关键词：

aspartimide; alpha-; beta-aspartyl peptides; solid-phase protocols; peptide synthesis protocols; SPPS protocols; beta-aspartyl methyl esters;

D O I：

10.1016/j.tetlet.2003.09.163

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Aspartimide formation is still an unresolved problem in the solid-phase peptide synthesis of aspartic acid-containing peptides, following either Boc- or Fmoc-based synthetic strategies. alpha-Aspartyl peptides of high purity can be obtained, despite aspartimide formation, by incorporating an additional step in the Boc- and Fmoc-based solid-phase peptide synthesis protocols, consisting of treatment of the peptide-resin with methanol in the presence of 2% DIEA (v/v) for 15 min immediately after completion of the peptide chain elongation. (C) 2003 Elsevier Ltd. All rights reserved.

引用

页码：8673 / 8676

页数：4

共 13 条

[1]

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[2]

BODANSZKY M, 1978, INT J PEPT PROT RES, V12, P69

[3]

BODANSZKY M, 1978, INT J PEPT PROT RES, V12, P57

[4] PIPERIDINE-MEDIATED SIDE PRODUCT FORMATION FOR ASP(OBU(T))-CONTAINING PEPTIDES [J].