The aspartimide problem in Fmoc-based SPPS.: Part II

被引：56

作者：

Mergler, M ^{[1
]}

Dick, F ^{[1
]}

Sax, B ^{[1
]}

Stähelin, C ^{[1
]}

Vorherr, T ^{[1
]}

机构：

[1] BACHEM AG, CH-4416 Budendorf, Switzerland

来源：

JOURNAL OF PEPTIDE SCIENCE | 2003年 / 9卷 / 08期

关键词：

aspartimide formation; backbone protection; Fmoc-solid phase peptide synthesis; Fmoc cleavage; Asp(OMpe);

D O I：

10.1002/psc.473

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：

The sequence dependence of base-catalysed aspartimide formation during Fmoc-based SPPS was systematically studied employing the peptide models H-Val-Lys-Asp-Xaa-Tyr-Ile-OH. The extent of formation of aspartimide and related by-products was determined by RP-HPLC. Considerable amounts of by-products were formed in the case of Xaa = Asp(OtBu), Arg(Pbf), Asn(Mtt), Cys(Acm) and unprotected Thr. Aspartimide formation could be diminished by incorporation of Asp(OMpe) or by employing milder methods for Fmoc cleavage, e.g. hexamethyleneimine/N-methylpyrrolidine/HOBt/NMP/DMSO 4:50:4:71:71 (v/v/w/v/v). Copyright (C) 2003 European Peptide Society and John Wiley Sons, Ltd.

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页码：518 / 526

页数：9

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