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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. [ABSTRACT FROM AUTHOR]

A series of novel 1,3-difunctionalized glycoconjugates were synthesized using a sequence of regioselective functionalization and stereoselective glycosidation of D-glucose and D-GlcNAc. Regioselective C-3 functionalization of sugar molecules was achieved by chemical functionalization of isopropylidene or oxazoline protected sugar derivatives. The structural diversity at the anomeric carbon was explored by stereoselective chemical glycosidation. The oxazoline protected D-GlcNAc derivative gave either pyranose or furanose derivatives on glycosidation depending on the amount of Lewis acid used. The diversely functionalized glycoconjugates with azide or alkyne groups are potentially useful for the synthesis of multifunctionalized complex glycoconjugates via click reactions. [ABSTRACT FROM AUTHOR]

Abstract In recent years, 1,4-triazole rings are being widely used for the synthesis of carbohydrate derived biomimetics, due to their easy synthesis and wide range of functional group compatibility. These triazole rings lead to synthetic molecules with improved enzymatic stability, bioavailability, and structural diversity. In this present work, a benzoyl group has been introduced at the C-5 position of the triazole ring present in the synthetic glycoconjugates providing further structural diversity to the molecule. 5-Benzoyl 1,4-triazole ring containing glycoconjugates were synthesized using Cu(I) catalyzed [3 + 2] cycloaddition reaction of per- O- acetylated glycopyranosyl azide and phenyl acetylene followed by in situ electrophilic addition of benzoyl group to the Cu(I) coordinated triazole intermediate. The X-ray crystal structure of one of the 5-benzoyl 1,4-triazole linked glycoconjugate derived from d -xylose {1- N -(2,3,4-tri- O -acetyl-β- d -xylopyranosyl)-4-phenyl-5-benzoyl-1,2,3-triazole} showed unique pattern of intermolecular C H...O interactions arranging the molecules in an anti-parallel orientation. The structure and morphology of the compounds were further explored using computational calculation and scanning electron microscopic (SEM) study which firmly established the uniqueness of 5-benzoyl 1,4-triazole linked glycoconjugates compared to that of 5-H 1,4-triazole linked derivative. Graphical abstract Image 1 Highlights • Single step synthesis of 5-benzoyl triazole linked glycoconjugates using [3 + 2] cycloaddition. • X-Ray crystal structure of one of the derivatives synthesized showed unique antiparallel arrangement of non-covalent interactions and DFT calculations showed good agreement with XRD data. • SEM study of the synthesized derivatives established the uniqueness of 5-benzoyl 1,4-triazole linked glycoconjugates compared to that of 5-H 1,4-triazole linked derivative. [ABSTRACT FROM AUTHOR]