title: How pure is your thiosialoside? A reinvestigation into the HPLC purification of thioglycosides of N-acetylneuraminic acid.
abstract: The synthesis of thiosialosides as potential biological probes for investigations involving the use of sialic acid-recognising proteins has been reinvestigated. It has been found that the most efficient method for the preparation of thiosialosides free from any 2,3-didehydro sialic acid contaminants involves an intermediate HPLC purification of thiosialosides as their methyl esters. Subsequent methyl ester hydrolysis provides thiosialosides (eg. 6 and 14) which are suitable for studies involving the use of sialic acid-recognising proteins.
authors.affiliation: Department of Medicinal Chemistry, Monash University (Parkville Campus), Victoria, Australia.
authors.forename: D R
authors.initials: DR
authors.lastname: Groves
authors.forename: S J
authors.initials: SJ
authors.lastname: Bradley
authors.forename: F J
authors.initials: FJ
authors.lastname: Rose
authors.forename: M J
authors.initials: MJ
authors.lastname: Kiefel
authors.forename: M
authors.initials: M
authors.lastname: von Itzstein
mesh_terms: D002851:Chromatography, High Pressure Liquid / Q000379:methods*; D019158:N-Acetylneuraminic Acid / Q000737:chemistry*; D012680:Sensitivity and Specificity; D012794:Sialic Acids / Q000737:chemistry; D013865:Thioglycosides / Q000737:chemistry*
chemical_list: D012794:Sialic Acids; D013865:Thioglycosides; D019158:N-Acetylneuraminic Acid