20702-82-3Relevant articles and documents
Thiazolidine Peracetates: Carbohydrate Derivatives that Readily Assign cis-, trans-2,3-Monosaccharides by Gas Chromatography-Mass Spectrometry Analysis
Price, Neil. P. J.,Hartman, Trina M.,Vermillion, Karl E.
, p. 8044 - 8050 (2018/06/25)
A novel group of carbohydrate derivatives is described that uniquely assign cis/trans-2,3-aldose stereoisomers at low nanomolar concentrations. Aldopentoses, aldohexoses, or component aldoses from hydrolysis of polysaccharides or oligosaccharides react with cysteamine in pyridine to give quantitative formation of thiazolidines, which are subsequently peracetylated in a one-pot reaction. The nonpolar thiazolidines peracetate (TPA) derivatives are analyzed by gas chromatography and electron impact mass spectrometry (GC/EI-MS), each aldose giving rise to two TPA geometric isomers. The quantitative ratio of these diastereomers is dependent upon whether the parent monosaccharide is cis-2,3-(Rib, Lyx, Man, All, Gul, and Tal), or trans-2,3-aldose (Xyl, Ara, Glc, Gal, Ido, and Alt). TPAs generate observed EI-MS fragment ions characteristic of C1-C2 and C3-C4 bond cleavage of the parent sugars. This has been used to estimate the extent of metabolic labeling of microbial cell-wall carbohydrates, especially into the defining anomeric carbons and during aldolase / ketolase -catalyzed rearrangements.
Stereochemical control in the formation of thiazolidines from O-protected reducing sugars
Wadouchi,Beaupere,Uzan,Stasik,Ewing,Mackenzie
, p. 147 - 154 (2007/10/02)
A synthetic procedure for the formation of thiazolidines from O-protected reducing sugars is described. The procedure allows access to five variations in the pattern of the protecting groups in the thiazolidine derived from D-mannose whilst maintaining co
