N-2 HYDROXY-4-METHOXYBENZYL (HMB) BACKBONE PROTECTION STRATEGY PREVENTS DOUBLE ASPARTIMIDE FORMATION IN A DIFFICULT PEPTIDE SEQUENCE

被引：39

作者：

PACKMAN, LC

机构：

[1] Cambridge Centre for Molecular Recognition, Department of Biochemistry, University of Cambridge, Cambridge, CB2 1QW, Tennis Court Road

来源：

TETRAHEDRON LETTERS | 1995年 / 36卷 / 41期

关键词：

D O I：

10.1016/0040-4039(95)01522-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Synthesis of an N-terminal, 20 residue fragment of ferredoxin by Fmoc-tert-butyl strategy gave a product in which both aspartic acid residues in an Asp-Gly-Asp-Asn sequence were converted to aspartimide. Resynthesis of the peptide using N-2-hydroxy-4-methoxybenzyl (Hmb) backbone protection at each Asp-Xaa peptide bond resulted in near-complete suppression of this side reaction.

引用

页码：7523 / 7526

页数：4

共 4 条

[1] SUPPRESSION OF PIPERIDINE-MEDIATED SIDE PRODUCT FORMATION FOR ASP(OBU(T))-CONTAINING PEPTIDES BY THE USE OF N-(2-HYDROXY-4-METHOXYBENZYL) (HMB) BACKBONE AMIDE PROTECTION
QUIBELL, M
OWEN, D
PACKMAN, LC
JOHNSON, T
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (20) : 2343 - 2344
[2] ROLES OF ELECTROSPRAY MASS-SPECTROMETRY, COUNTERION DISTRIBUTION MONITORING AND N-(2-HYDROXY-4-METHOXYBENZYL) BACKBONE PROTECTION IN PEPTIDE-SYNTHESIS
PACKMAN, LC
QUIBELL, M
JOHNSON, T
PEPTIDE RESEARCH, 1994, 7 (03): : 125 - 131
[3] IMPROVED PREPARATION OF BETA-AMYLOID(1-43) - STRUCTURAL INSIGHT LEADING TO OPTIMIZED POSITIONING OF N-(2-HYDROXY-4-METHOXYBENZYL) (HMB) BACKBONE AMIDE PROTECTION
QUIBELL, M
TURNELL, WG
JOHNSON, T
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1995, (16): : 2019 - 2024
[4] On-resin solid-phase synthesis of asparagine N-linked glycopeptides: Use of N-(2-acetoxy-4-methoxybenzyl) (AcHmb) aspartyl amide-bond protection to prevent unwanted aspartimide formation
Offer, J
Quibell, M
Johnson, T
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1996, (02): : 175 - 182

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