Synthesis and conformational analysis of phosphorylated β-(1→2) linked mannosides

9 p.-2 tab.-6 fig.
Phosphorylated β-(1→2)-oligomannosides are found on the cell surface of several Candida species, including Candida albicans (an opportunistic pathogen). These molecules are believed to take part in the invasion process of fungal infections, which in the case of C. albicans can lead to severe bloodstream infections and death, and can therefore be considered important from a biological standpoint. Understanding the mechanism of their action requires access to the corresponding oligosaccharide model compounds in pure form. In the present work, synthesis of the model core structures involved in the invasion process of C. albicans, consisting of phosphorylated β-(1→2)-linked mannotriose and tetraose, is reported. In order to elucidate the nature of these molecules in more detail, an extensive NMR-spectroscopic study encompassing complete spectral characterization, conformational analysis and molecular modelling was performed. The obtained results were also compared to similar chemical entities devoid of the charged phosphate group.
The authors thank the Academy of Finland (Research Grant #252371) and Stiftelsens för Åbo Akademi Forskningsinstitut for financial support. The CMST COST Action CM1102 Multivalent Glycosystems for Nanoscience—MultiGlycoNano is thanked for STSM funding to J.R., who also further acknowledges Suomalaisten Kemistien Seura for Young Scientist Award granted for his M.Sc. thesis work based on this study.