title: Synthesis of octyl 2-O-alpha-D-mannopyranosyl-alpha-D-mannopyranoside, its 6'-phosphate and the corresponding monomethyl phosphodiester: intermediate structures in the biosynthesis of N-linked oligosaccharides in Dictyostelium discoidium.
abstract: Octyl 2-O-alpha-D-mannopyranosyl-alpha-D-mannopyranoside, its 6'-phosphate and the corresponding 6'-methyl phosphodiester have been chemically synthesized. The latter compound was prepared using an H-phosphonate intermediate. These structures are for use as enzyme substrates and reference standards in a study on the biosynthesis of phosphorylated N-linked glycoproteins in the amoebae Dictyostelium discoideum.
authors.affiliation: Department of Chemistry, University of Alberta, Edmonton, Canada.
authors.forename: C
authors.initials: C
authors.lastname: Hällgren
authors.forename: O
authors.initials: O
authors.lastname: Hindsgaul
mesh_terms: D000818:Animals; D002240:Carbohydrate Sequence; D004023:Dictyostelium / Q000378:metabolism*; D004187:Disaccharides / Q000138:chemical synthesis*; D006023:Glycoproteins / Q000096:biosynthesis*; D008362:Mannosides / Q000138:chemical synthesis*; D008969:Molecular Sequence Data; D010750:Phosphoproteins / Q000096:biosynthesis*; D013403:Sugar Phosphates / Q000138:chemical synthesis
chemical_list: D004187:Disaccharides; D006023:Glycoproteins; D008362:Mannosides; D010750:Phosphoproteins; D013403:Sugar Phosphates; C088900:octyl 2-O-mannopyranosylmannopyranoside; C088901:octyl 2-O-(mannopyranosyl-6-phosphate)mannopyranoside; C088902:octyl 2-O-(mannopyranosyl-6-methylphosphate)mannopyranoside