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

A1 Journal article (refereed)


Internal Authors/Editors


Publication Details

List of Authors: Jani Rahkila, Filip S. Ekholm, Rajib Panchadhayee, Ana Ardá, Francisco Javier Cañada, Jesús Jiménez-Barbero, Reko Leino
Publisher: Elsevier
Publication year: 2014
Journal: Carbohydrate Research
Volume number: 383
Start page: 58
End page: 68


Abstract

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.


Keywords

Carbohydrates, Molecular modeling, NMR spectroscopy, oligosaccharide synthesis, organic chemistry

Last updated on 2019-21-10 at 04:20