Synthesis of oligosaccharides related to galactomannans from Aspergillus fumigatus and their NMR spectral data

Abstract

The synthesis of model oligosaccharides related to antigenic galactomannans of the dangerous fungal pathogen Aspergillus fumigatus has been performed employing pyranoside-into-furanoside (PIF) rearrangement and controlled O(5) → O(6) benzoyl migration as key synthetic methods. The prepared compounds along with some previously synthesized oligosaccharides were studied by NMR spectroscopy with the full assignment of ¹H and ¹³C signals and the determination of ¹³C NMR glycosylation effects. The obtained NMR database on ¹³C NMR chemical shifts for oligosaccharides representing galactomannan fragments forms the basis for further structural analysis of galactomannan related polysaccharides by a non-destructive approach based on the calculation of the ¹³C NMR spectra of polysaccharides by additive schemes.