title: Synthesis of zwitterionic 1,1'-glycosylphosphodiester: a partial structure of galactosamine-modified Francisella lipid A.
abstract: Synthesis of a "double glycosidic" phosphodiester comprising anomeric centers of two 2-amino-2-deoxy-sugars is reported. The carbohydrate epitope of Francisella lipid A modified with α-d-galactosamine at the anomerically linked phosphate has been stereoselectively prepared and coupled to maleimide-activated bovine serum albumin via an amide-linked thiol-terminated spacer group. H-Phosphonate and phosphoramidite approaches have been explored for the coupling of 4,6-DTBS-2-azido-protected GalN lactol and peracetylated spacer-equipped reducing βGlcN(1→6)GlcN disaccharide via phosphodiester linkage. Deprotection conditions preserving the integrity of the labile glycosidic zwitterionic phosphodiester were elaborated.
authors.affiliation: Department of Chemistry, University of Natural Resources and Life Sciences , Muthgasse 18, A-1190 Vienna, Austria.
authors.forename: David
authors.initials: D
authors.lastname: Baum
authors.forename: Paul
authors.initials: P
authors.lastname: Kosma
authors.forename: Alla
authors.initials: A
authors.lastname: Zamyatina
mesh_terms: D004187:Disaccharides / Q000737:chemistry; D005603:Francisella / Q000737:chemistry*; D005688:Galactosamine / Q000737:chemistry / Q000378:metabolism*; D008050:Lipid A / Q000138:chemical synthesis / Q000737:chemistry*; D015394:Molecular Structure; D010755:Organophosphates / Q000138:chemical synthesis / Q000737:chemistry
chemical_list: D004187:Disaccharides; D008050:Lipid A; D010755:Organophosphates; D005688:Galactosamine