Click mediated synthesis of functionalized glycolipids with peptide-peptoid linkages

The present work describes the synthesis of a new class of glycolipids with systematic variations 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. 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 analysed by comparing their self-assemblies 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.

Automated summary

This work describes the synthesis of a new class of glycolipids with structural diversity in the linkage region and the aglycon part. The glycolipids were synthesized using Cu(I) catalyzed click reaction and incorporated diverse peptide foldamer groups. The synthesized glycolipids were characterized and the impact of different bonds on their morphology was analyzed.