152203-03-7Relevant articles and documents
Stereoselective innovative synthesis and biological evaluation of new real carba analogues of minimal epitope Manα(1,2)Man as DC-SIGN inhibitors
Bordoni, Vittorio,Porkolab, Vanessa,Sattin, Sara,Thépaut, Michel,Frau, Ileana,Favero, Lucilla,Crotti, Paolo,Bernardi, Anna,Fieschi, Franck,Di Bussolo, Valeria
, p. 89578 - 89584 (2016)
Antagonists of the C-type lectin DC-SIGN are promising therapeutic agents against viruses and bacteria. The development of glycomimetic ligands for DC-SIGN has so far proved to be challenging, since this membrane-protein presents four carbohydrate-binding domains (CRD) that specifically recognize mannose and fucose. In the recent past, we were able to develop inhibitors mimicking the minimal natural epitope Manα(1,2)Man using a mannoside with conformationally restricted dimethyl cycloexandicarboxylate-based aglycons designed to exploit the high enzymatic stability and to generate multivalent or solid supported systems as potent lectin ligands. Herein we describe the innovative synthesis of a different class of pseudodisaccharides, mimics of the natural Manα(1,2)Man moiety, characterized by the presence of a real d-carbamannose unit instead of a simpler mimic structure. Their chemical synthesis and biological activity using an SPR inhibition assay are reported. These pseudodisaccharides display inhibition values similar to those of the natural disaccharide Manα(1,2)Man, with a good affinity for DC-SIGN and can be considered as possible candidates for further structural modifications towards improved inhibitors.
Synthesis and Glycosidase-inhibitory Activity of Cyclophellitol Analogues
Tai, Vincent W.-F.,Fung, P.-H.,Wong, Y.-S.,Shing, Tony K. M.
, p. 1353 - 1362 (1994)
The 6-deoxy-1,2-anhydro-analogues of cyclophellitol, 5 and 6, have been synthesised from diol 11 via regioselective ring opening of the cyclic sulfate 15, an internal SN2 reaction and hydrogenolysis.Compounds 5,6, cyclophellitol 1 and its diast
Chemoenzymatic syntheses of carbasugar analogues of nucleoside diphosphate sugars: UDP-carba-Gal, UDP-carba-GlcNAc, UDP-carba-Glc, and GDP-carba-Man
Seo, Kyung-Chang,Kwon, Young-Geol,Kim, Dae-Hee,Jang, In-Sook,Cho, Jin-Won,Chung, Sung-Kee
supporting information; experimental part, p. 1733 - 1735 (2009/08/08)
Chemoenzymatic syntheses of several NDP-carba-sugars have been successfully carried out, and these essential cofactor analogues are expected to be selective inhibitors of glycosyltransferase enzymes. The Royal Society of Chemistry.
Synthesis of carboxylic analogues of the mannosyl trisaccharide: ether- and imino-linked methyl 3,6-bis(5a-carba-α-D-mannopyranosyl)-3,6-dideoxy-α-D-mannopyranosides
Ogawa, Seiichiro,Sasaki, Shin-ichi,Tsunoda, Hidetoshi
, p. 183 - 196 (2007/10/02)
Carboxylic analogues 2 and 3 of the "trimannosyl structure 1", methyl 3,6-bis(5a-carba-α-D-mannopyranosyl)-3,6-dideoxy-α-D-mannopyranosides bonded by way of respective ether and imino linkages, were synthesized.The ether 2 had no inhibitory activity again