Comparison of the Self-Assembly and Conformations of Glucose- and Galactose-Based Glycopyranosides in Dilute Aqueous Solution.

ABSTRACT: A series of glycolipids (glycopyranosides) was prepared by coupling glucosamine or galactosamine (at the C₂ position) with myristic (tetradecanoic) or palmitic (hexadecanoic) acid. The conformation and self-assembly were examined in aqueous solutions containing 10% methanol. Circular dichroism and FTIR spectroscopy reveal notable differences in the chiral ordering and conformation comparing analogues with glucose and galactose "headgroups". A glucose derivative (to palmitic acid) was also prepared with a different (C₁-) substitution position of the lipid chain, and this was found to significantly influence chiral ordering and conformation. The self-assembly of the glycolipids was examined using cryogenic-transmission electron microscopy (cryo-TEM) and small-angle X-ra

SUBMITTER: Hamley IW 

PROVIDER: S-EPMC12461907 | biostudies-literature | 2025 Sep

REPOSITORIES: biostudies-literature