title: Synthesis of O- and C-glycosides derived from β-(1,3)-D-glucans.
abstract: A series of β-(1,3)-d-glucans have been synthesized incorporating structural variations specifically on the reducing end of the oligomers. Both O- and C-glucosides derived from di- and trisaccharides have been obtained in good overall yields and with complete selectivity. Whereas the O-glycosides were obtained via a classical Koenigs-Knorr glycosylation, the corresponding C-glycosides were obtained through allylation of the anomeric carbon and further cross-metathesis reaction. Finally, the compounds were evaluated against two glycosidases and two endo-glucanases and no inhibitory activity was observed.
authors.affiliation: Laboratorio de Síntesis Asimétrica, Departamento de Síntesis y Estructura de Biomoléculas, Instituto de Síntesis Química y Catálisis Homogénea (ISQCH), Universidad de Zaragoza, CSIC, 50009 Zaragoza, Aragón, Spain. Electronic address: emarca@unizar.es.
authors.forename: Eduardo
authors.initials: E
authors.lastname: Marca
authors.forename: Jessika
authors.initials: J
authors.lastname: Valero-Gonzalez
authors.forename: Ignacio
authors.initials: I
authors.lastname: Delso
authors.forename: Tomás
authors.initials: T
authors.lastname: Tejero
authors.forename: Ramon
authors.initials: R
authors.lastname: Hurtado-Guerrero
authors.forename: Pedro
authors.initials: P
authors.lastname: Merino
mesh_terms: D002240:Carbohydrate Sequence; D002480:Cellulase / Q000037:antagonists & inhibitors; D060326:Chemistry Techniques, Synthetic; D048013:Acetivibrio thermocellus / Q000201:enzymology; D004187:Disaccharides / Q000737:chemistry; D004791:Enzyme Inhibitors / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D005936:Glucans / Q000737:chemistry*; D006026:Glycoside Hydrolases / Q000037:antagonists & inhibitors; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D006031:Glycosylation; D001467:Hordeum / Q000201:enzymology; D057927:Hydrophobic and Hydrophilic Interactions; D008969:Molecular Sequence Data; D009005:Monosaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D011134:Polysaccharides / Q000737:chemistry; D013329:Structure-Activity Relationship; D014312:Trisaccharides / Q000737:chemistry
chemical_list: C438934:C-glycoside; D004187:Disaccharides; D004791:Enzyme Inhibitors; D005936:Glucans; D006027:Glycosides; D009005:Monosaccharides; D011134:Polysaccharides; D014312:Trisaccharides; C014637:laminaribiose; C008247:laminaran; D006026:Glycoside Hydrolases; D002480:Cellulase
keywords: Fungal infections; Glucans; Laminarans; Laminaribiose; Laminaritriose