Efficient Construction of Proline-Containing β-Turn Mimetic Cyclic Tetrapeptides via CuAAC Macrocyclization

被引：35

作者：

Chouhan, Gagan ^{[1
]}

James, Keith ^{[1
]}

机构：

[1] Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA

来源：

ORGANIC LETTERS | 2013年 / 15卷 / 06期

关键词：

PROTEIN-PROTEIN INTERACTIONS; AZIDE-ALKYNE CYCLOADDITIONS; RING-CLOSING METATHESIS; CLICK CHEMISTRY; LINEAR PEPTIDES; DRUG DISCOVERY; BIOLOGICAL-ACTIVITY; PEPTIDOMIMETICS; MIMICS; PERMEABILITY;

D O I：

10.1021/ol303572t

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A range of macrocyclic beta-turn mimetic tetrapeptides was prepared by efficient copper-tris(triazole) ligand complex catalyzed azide-alkyne "click" macrocyclizations in good to high yields. Preliminary conformational studies using X-ray crystallography and NMR spectroscopy demonstrated the presence of intramolecular H-bonds characteristic of beta-turns in these cyclic tetrapeptides.

引用

页码：1206 / 1209

页数：4

共 78 条

[31] Large structural modification with conserved conformation:: Analysis of Δ3-fused aryl prolines in model β-turns [J].