title: Syntheses of phosphatidyl-beta-D-glucoside analogues to probe antigen selectivity of monoclonal antibody 'DIM21'.
abstract: Herein, we report the chemical syntheses of a series of phosphatidyl-beta-D-glucoside (PtdGlc) analogues, including 6-O-Ac, sn-2-O-Me, phosphorothioate as well as phosphatidylgalactoside and -mannoside derivatives. In the key step, beta-glycosyl H-phosphonate was condensed with enantiomerically pure diacylglycerol. Comparison of spectroscopic data with mono-acetylated PtdGlc from natural source confirmed the presence of an acetyl moiety at position 6. Furthermore, the reactivity of PtdGlc and its analogues toward monoclonal antibody 'DIM21' (MAb DIM21) was evaluated, revealing the crucial structural antigen features for successful MAb DIM21 binding.
authors.affiliation: RIKEN, The Institute of Physical and Chemical Research, Advanced Science Institute, 2-1 Hirosawa, Wako, Saitama 351-0198, Japan.
authors.forename: Peter
authors.initials: P
authors.lastname: Greimel
authors.forename: Milaine
authors.initials: M
authors.lastname: Lapeyre
authors.forename: Yasuko
authors.initials: Y
authors.lastname: Nagatsuka
authors.forename: Yoshio
authors.initials: Y
authors.lastname: Hirabayashi
authors.forename: Yukishige
authors.initials: Y
authors.lastname: Ito
mesh_terms: D000911:Antibodies, Monoclonal / Q000737:chemistry / Q000276:immunology*; D000918:Antibody Specificity; D000936:Antigen-Antibody Complex; D000941:Antigens; D002236:Carbohydrate Conformation; D020404:Glycerophospholipids / Q000737:chemistry* / Q000276:immunology*; D008958:Models, Molecular; D013329:Structure-Activity Relationship
chemical_list: D000911:Antibodies, Monoclonal; D000936:Antigen-Antibody Complex; D000941:Antigens; D020404:Glycerophospholipids; C429823:phosphatidylglucose