title: Functional glycolipid-crown-ethers by click chemistry.
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.
authors: Chemistry Department, Faculty of Science, University of Malaya, Lembah Pantai, 50603 Kuala Lumpur, Malaysia.
authors: Abbas Abdulameer
authors: AA
authors: Salman
authors: Chemistry Department, Faculty of Science, University of Malaya, Lembah Pantai, 50603 Kuala Lumpur, Malaysia.
authors: Mojtaba
authors: M
authors: Tabandeh
authors: Chemistry Department, Faculty of Science, University of Malaya, Lembah Pantai, 50603 Kuala Lumpur, Malaysia. Electronic address: heidelberg@um.edu.my.
authors: Thorsten
authors: T
authors: Heidelberg
authors: Chemistry Department, Faculty of Science, University of Malaya, Lembah Pantai, 50603 Kuala Lumpur, Malaysia.
authors: Rusnah Syahila
authors: RS
authors: Duali Hussen
mesh_terms: D001386:Azides / Q000737:chemistry; D057930:Click Chemistry; D043844:Crown Ethers / Q000138:chemical synthesis*; D003500:Cyclization; D006017:Glycolipids / Q000138:chemical synthesis*; D008958:Models, Molecular; D013501:Surface-Active Agents / Q000138:chemical synthesis
chemical_list: D001386:Azides; D043844:Crown Ethers; D006017:Glycolipids; D013501:Surface-Active Agents
keywords: Alkali complexation; Copper-catalyzed azide-alkyne cycloaddition (CuAAC); Surfactant assembly; Triazole-linked macrocyclic ligand