'O-Acyl isopeptide method' for peptide synthesis:: Solvent effects in the synthesis of Aβ1-42 isopeptide using 'O-acyl isodipeptide unit'

被引：26

作者：

Taniguchi, Atsuhiko ^{[1
]}

Yoshiya, Taku ^{[1
]}

Abe, Naoko ^{[1
]}

Fukao, Fukue ^{[1
]}

Sohma, Youhei ^{[1
,2
]}

Kimura, Tooru ^{[1
]}

Hayashi, Yoshio ^{[1
,3
]}

Kiso, Yoshiaki ^{[1
]}

机构：

[1] Kyoto Pharmaceut Univ, Century COE Program 21, Ctr Frontier Res Med Sci, Dept Med Chem,Yamashina Ku, Kyoto 6078412, Japan

[2] Kyoto Pharmaceut Univ, Century COE Program 21, Ctr Frontier Res Med Sci, Dept Pharmaceut Mfg Chem,Yamashina Ku, Kyoto 6078412, Japan

[3] Tokyo Univ Pharm & Life Sci, Sch Pharm, Dept Med Chem, Tokyo 1920392, Japan

来源：

JOURNAL OF PEPTIDE SCIENCE | 2007年 / 13卷 / 12期

关键词：

O-acyl isodipeptide unit; O-acyl isopeptide method; amyloid P peptide; difficult sequence-containing peptide; solvent effect;

D O I：

10.1002/psc.905

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

'O-Acyl isopeptide method' is an efficient synthetic method for peptides. We designed 'O-acyl isodipeptide units', Boc-Ser/Thr(Fmoc-Xaa)-OH, as important building blocks to enable routine use of the O-acyl isopeptide method. In the synthesis of an A beta 1-42 isopeptide using O-acyl isodipeptide unit Boe-Ser(Fmoc-Gly)-OH, a side reaction, resulting in the deletion of Ser(26) in the O-acyl isopeptide structure, was noticed during coupling of the unit. We observed that the side reaction occurred during the activation step and was solvent-dependent. In DMF or NMIP, an intramolecular side reaction, originating from the activated species of the unit, occurred during the activation step. In non-polar solvents such as CHCl3 or CH2Cl2, the side reaction was less likely to occur. Using CH2Cl2 as solvent in coupling the unit, the target A beta 1-42 isopeptide was synthesized with almost no major side reaction. Copyright (c) 2007 European Peptide Society and John Wiley & Sons, Ltd.

引用

页码：868 / 874

页数：7

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