IMPROVED PREPARATION OF BETA-AMYLOID(1-43) - STRUCTURAL INSIGHT LEADING TO OPTIMIZED POSITIONING OF N-(2-HYDROXY-4-METHOXYBENZYL) (HMB) BACKBONE AMIDE PROTECTION

被引：23

作者：

QUIBELL, M ^{[1
]}

TURNELL, WG ^{[1
]}

JOHNSON, T ^{[1
]}

机构：

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

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1995年 / 16期

关键词：

D O I：

10.1039/p19950002019

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We report an improved synthetic strategy for the preparation of the amyloidogenic protein fragment beta-amyloid(1-43). The scheme is based upon the generation of highly soluble N-(2-hydroxy-4-methoxybenzyl) (Hmb) backbone amide-protected intermediates. Optimal positioning of backbone protection at glycines(25,29,33,37) together with phenylalanine(20), was determined from a beta-hairpin model derived for the C-terminal region of the resin-bound peptide. This improved scheme provides the final product in 28% overall yield.

引用

页码：2019 / 2024

页数：6

共 3 条

[1] PREPARATION AND PURIFICATION OF BETA-AMYLOID(1-43) VIA SOLUBLE, AMIDE BACKBONE PROTECTED INTERMEDIATES
QUIBELL, M
TURNELL, WG
JOHNSON, T
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (07): : 1745 - 1750
[2] 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
[3] 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

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