Functional glycolipid-crown-ethers by click chemistry. (10th April 2015)

• Record Type: Journal Article
• Authors: Salman, Abbas Abdulameer; Tabandeh, Mojtaba; Heidelberg, Thorsten; Duali Hussen, Rusnah Syahila
• Is Part Of: Carbohydrate research. Volume 406(2015)
• Page Start: 41
• Page End: 45
• Publication Date: 2015-04-10
• Subjects: Triazole-linked macrocyclic ligand -- Copper-catalyzed azide-alkyne cycloaddition (CuAAC) -- Surfactant assembly -- Alkali complexation; Carbohydrates -- Periodicals; Chemistry, Organic -- Periodicals; Biochemistry -- Periodicals; Carbohydrates -- Periodicals; Chimie organique -- Périodiques; Glucides -- Périodiques; Biochemistry; Carbohydrates; Chemistry, Organic; Periodicals; Electronic journals; 507.78
• DOI: 10.1016/j.carres.2014.12.015
• Languages: English
• ISSNs: 0008-6215

Abstract

Abstract: A series of glycolipid crown ether analogs was prepared by bis-propargylation of lauryl glycoside followed by subsequent click-coupling with ethylene glycol-based diazides. The triazole-linked macrocycles were obtained in remarkable high yields. While the surfactant assembly was affected by presence of sodium ions, suggesting the formation of complexes, no ion-selectivity was observed for the macrocylic ligands. Computational studies suggest a low but significant cation-binding activity of the macrocycle, involving coordination at both oxygen and nitrogen atoms. Graphical abstract: Highlights: Click chemistry enables efficient anellation of macrocyclic ligands on glycolipids. Electrolytes increase CMC of glycolipids with CuAAC-based crown-ether-anellation. Triazole-containing crown-ether analogs do not enable selective alkali complexation.