title: Synthesis and conformational analysis of phosphorylated β-(1→2) linked mannosides.
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.
authors.affiliation: Laboratory of Organic Chemistry, Åbo Akademi University, FI-20500 Åbo, Finland.
authors.forename: Jani
authors.initials: J
authors.lastname: Rahkila
authors.affiliation: Laboratory of Organic Chemistry, Åbo Akademi University, FI-20500 Åbo, Finland; Glykos Finland Ltd, Viikinkaari 6, 00790 Helsinki, Finland.
authors.forename: Filip S
authors.initials: FS
authors.lastname: Ekholm
authors.affiliation: Laboratory of Organic Chemistry, Åbo Akademi University, FI-20500 Åbo, Finland.
authors.forename: Rajib
authors.initials: R
authors.lastname: Panchadhayee
authors.affiliation: Centro de Investigaciones Biológicas, Ramiro de Maeztu 9, 28040 Madrid, Spain.
authors.forename: Ana
authors.initials: A
authors.lastname: Ardá
authors.affiliation: Centro de Investigaciones Biológicas, Ramiro de Maeztu 9, 28040 Madrid, Spain.
authors.forename: Francisco Javier
authors.initials: FJ
authors.lastname: Cañada
authors.affiliation: Centro de Investigaciones Biológicas, Ramiro de Maeztu 9, 28040 Madrid, Spain.
authors.forename: Jesús
authors.initials: J
authors.lastname: Jiménez-Barbero
authors.affiliation: Laboratory of Organic Chemistry, Åbo Akademi University, FI-20500 Åbo, Finland. Electronic address: reko.leino@abo.fi.
authors.forename: Reko
authors.initials: R
authors.lastname: Leino
mesh_terms: D002176:Candida albicans / Q000737:chemistry* / Q000472:pathogenicity; D058365:Candidiasis, Invasive / Q000188:drug therapy* / Q000209:etiology; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D008362:Mannosides / Q000138:chemical synthesis* / Q000737:chemistry; D010766:Phosphorylation; D014312:Trisaccharides / Q000138:chemical synthesis* / Q000737:chemistry / Q000302:isolation & purification
chemical_list: D008362:Mannosides; D014312:Trisaccharides; C023872:mannotriose
keywords: Carbohydrates; Molecular modelling; NMR-spectroscopy; Oligosaccharides; Organic synthesis