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

被引：66

作者：

QUIBELL, M

OWEN, D

PACKMAN, LC

JOHNSON, T

机构：

[1] MRC,MOLEC BIOL LAB,CAMBRIDGE CB2 2QH,ENGLAND

[2] UNIV CAMBRIDGE,DEPT BIOCHEM,CAMBRIDGE CB2 1QW,ENGLAND

来源：

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS | 1994年 / 20期

关键词：

D O I：

10.1039/c39940002343

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Piperidine-mediated aspartimide and subsequent piperidide formation, during Fmoc-based synthesis of sensitive aspartyl (beta-tert-butyl ester, OBu(t))-containing peptides, is completely suppressed by the use of Hmb protection of the aspartyl amide bond.

引用

页码：2343 / 2344

页数：2

共 6 条

[1] PIPERIDINE-MEDIATED SIDE PRODUCT FORMATION FOR ASP(OBU(T))-CONTAINING PEPTIDES
DOLLING, R
BEYERMANN, M
HAENEL, J
KERNCHEN, F
KRAUSE, E
FRANKE, P
BRUDEL, M
BIENERT, M
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (07) : 853 - 854
[2] 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
[3] REVERSIBLE MODIFICATION OF THE ACID-LABILE 2-HYDROXY-4-METHOXYBENZYL (HMB) AMIDE PROTECTING GROUP - A SIMPLE SCHEME YIELDING BACKBONE SUBSTITUTED FREE PEPTIDES
QUIBELL, M
TURNELL, WG
JOHNSON, T
TETRAHEDRON LETTERS, 1994, 35 (14) : 2237 - 2238
[4] 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
[5] N-2 HYDROXY-4-METHOXYBENZYL (HMB) BACKBONE PROTECTION STRATEGY PREVENTS DOUBLE ASPARTIMIDE FORMATION IN A DIFFICULT PEPTIDE SEQUENCE
PACKMAN, LC
TETRAHEDRON LETTERS, 1995, 36 (41) : 7523 - 7526
[6] 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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