结构预组织的二价碳水化合物的复分解反应。大环和低聚物支架的合成。

Metathesis of structurally preorganized bivalent carbohydrates. Synthesis of macrocyclic and oligomeric scaffolds.

作者信息

Velasco-Torrijos Trinidad, Murphy Paul V

机构信息

Centre for Synthesis and Chemical Biology, Chemistry Department, Conway Institute of Biomolecular and Biomedical Research, University College Dublin, Belfield, Dublin 4, Ireland.

出版信息

Org Lett. 2004 Oct 28;6(22):3961-4. doi: 10.1021/ol0484254.

DOI:10.1021/ol0484254

PMID:15496074

Abstract

[reaction: see text] Bivalent carbohydrate substrates for metathesis were synthesized from glucuronic acid and phenylene-1,4-diamine. The substrate secondary structure depends on whether secondary or tertiary amides are present, and this influences the course of the metathesis reaction leading to novel multivalent scaffolding. Molecular modeling suggests that a very rigid macrocyclic scaffold has potential for the development of alpha-helix peptidomimetics.

摘要

[反应：见正文] 用于复分解反应的二价碳水化合物底物由葡萄糖醛酸和对苯二胺合成。底物的二级结构取决于二级酰胺或三级酰胺是否存在，这会影响导致新型多价支架的复分解反应进程。分子模拟表明，一种非常刚性的大环支架具有开发α-螺旋肽模拟物的潜力。