Click mediated synthesis of functionalized glycolipids with peptide-peptoid linkages

Abstract

The present work describes the synthesis of a new class of glycolipids with systematic variation in the linkage region as well as in the aglycon part using Cu(I) catalyzed click reaction. The linkage region between sugar and the aglycon part was diversified using amide, amido-triazole, and 5-benzoyl triazole moieties. The structural diversity of glycolipids was further amplified by incorporating several polar peptide foldamer groups such as triazole, amide, peptide, or N-aryl peptoid in the aglycon part of it. The newly designed glycolipids were derived from the amalgamation of different peptide bond mimics. This work reports the first use of N-aryl peptoid in the synthesis of glycolipids. The newly synthesized glycolipids were characterized using different spectroscopic and spectrometric analyses. The impact of the amide bond as well as the triazole ring in the linkage region on the morphology of the glycolipids was analyzed by comparing their self-assembly using SEM analysis. The geometries of the glycolipids were also optimized using density functional theory and the optimized structures were found to be minima in the potential energy surfaces.