Synthesis and NMR elucidation of novel pentacycloundecane-based peptides

被引：6

作者：

Altaib, Mohamed S. ^{[1
]}

Arvidsson, Per I. ^{[2
,3
]}

Govender, Thavendran ^{[4
]}

Maguire, Glenn E. M. ^{[1
]}

Makatini, Maya ^{[1
]}

Onajole, Oluseye K. ^{[1
]}

Kruger, Hendrik G. ^{[1
]}

机构：

[1] Univ KwaZulu Natal, Sch Chem, ZA-4001 Durban, South Africa

[2] Uppsala Univ, Dept Biochem & Organ Chem, S-75123 Uppsala, Sweden

[3] AstraZeneca R&D Sodertalje, Discovery CNS & Pain Control, S-15185 Sodertalje, Sweden

[4] Univ KwaZulu Natal, Sch Pharm & Pharmacol, ZA-4001 Durban, South Africa

来源：

MAGNETIC RESONANCE IN CHEMISTRY | 2010年 / 48卷 / 06期

基金：

新加坡国家研究基金会;

关键词：

PCU peptides; AVPI; 2D NMR; beta-turns; structure elucidation; TRISHOMOCUBANE AMINO-ACID; MOLECULAR-DYNAMICS; DERIVATIVES; DESIGN; ASSIGNMENT; CHEMISTRY; MIMETICS; RESIDUES; LIGANDS; POTENT;

D O I：

10.1002/mrc.2598

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The synthesis and NMR elucidation of two novel pentacycloundecane (PCU)-based peptides are reported. The PCU cage amino acids were synthesised as racemates and the incorporation of the cage amino acid with (S)-natural amino acids produced diastereomeric peptides. The diastereomeric 'cage' peptides were separated using preparative HPLC and the NMR elucidation of these PCU containing peptides are reported for the first time. The (1)H and (13)C NMR spectra showed series of overlapping signals of the cage skeleton and that of the peptide, making it extremely difficult to resolve the structure using one-dimensional NMR techniques only. The use of two-dimensional NMR techniques proved to be a highly effective tool in overcoming this problem. Copyright (C) 2010 John Wiley & Sons, Ltd.

引用

页码：435 / 442

页数：8

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