Synthesis and O-Glycosidic Linkage Conformational Analysis of ¹³C-Labeled Oligosaccharide Fragments of an Antifreeze Glycolipid.

ABSTRACT: NMR studies of two ¹³C-labeled disaccharides and a tetrasaccharide were undertaken that comprise the backbone of a novel thermal hysteresis glycolipid containing a linear glycan sequence of alternating [βXyl p-(1→4)-βMan p-(1→4)] _n dimers. Experimental trans-glycoside NMR J-couplings, parameterized equations obtained from density functional theory (DFT) calculations, and an in-house circular statistics package ( MA'AT) were used to derive conformational models of linkage torsion angles ϕ and ψ in solution, which were compared to those obtained from molecular dynamics simulations. Modeling using different probability distribution functions showed that MA'AT models of ϕ in βMan(1→4)βXyl and βXyl(1→4)βMan linkages are very similar in the disaccharide building blocks, whe

SUBMITTER: Zhang W 

PROVIDER: S-EPMC8224223 | biostudies-literature | 2019 Feb

REPOSITORIES: biostudies-literature