50271-46-0Relevant academic research and scientific papers
Syntheses of the 3- and 4-thio analogues of 4-nitrophenyl 2-acetamido-2-deoxy-β-d-gluco- and galactopyranoside
Chen, Hong-Ming,Withers, Stephen G.
, p. 2212 - 2222 (2008/02/12)
The syntheses of 4-nitrophenyl β-glycosides of the 3-thio and 4-thio analogues of the two principal 2-acetamido-2-deoxy-hexoses found in living systems, GlcNAc and GalNAc, are described. While synthesis of the 4-thio analogues could be achieved via nucleophilic displacements of sulfonate derivatives with thioacetate, problems with neighbouring group acetamido participation necessitated the use of sulfamidate intermediates for the 3-thio analogues. These 3- and 4-thio analogues are employed in the chemo-enzymatic synthesis of thio-oligosaccharide analogues of structures present in glycosaminoglycans, glycoproteins and glycolipids.
Synthesis and utility of sulfated chromogenic carbohydrate model substrates for measuring activities of mucin-desulfating enzymes
Clinch, Keith,Evans, Gary B,Furneaux, Richard H,Rendle, Phillip M,Rhodes, Phillippa L,Roberton, Anthony M,Rosendale, Douglas I,Tyler, Peter C,Wright, Damian P
, p. 1095 - 1111 (2007/10/03)
A chromogenic substrate, 4-nitrophenyl 2-acetamido-2-deoxy-β-D-glucopyranoside 6-sodium sulfate was synthesized and used in combination with β-N-acetylhexosaminidase for detection of the sulfatase, MdsA, by release of 4-nitrophenol. MdsA was originally isolated from the bacterium Prevotella strain RS2 and is believed to be involved in desulfation of sulfomucins, major components of the mucus barrier protecting the human colon surface. The exo nature of the MdsA sulfatase was indicated by its inability to de-esterify the disaccharide 4-nitrophenyl β-D-galactopyranosyl-(1→4)-2-acetamido-2-deoxy-β-D- glucopyranoside 6-sodium sulfate. This latter compound was prepared from monosaccharide precursors by two different methods, the shorter requiring just six steps from 4-nitrophenyl 2-acetamido-2-deoxy-β-D-glucopyranoside and giving an overall yield of 26.4%. The syntheses of 4-nitrophenyl β-D-galactopyranoside 3-triethylammonium sulfate and 6-triethylammonium sulfate and their use in combination with β-galactosidase as chromogenic substrates for detecting Bacteroides fragilis sulfatases with different specificities was also demonstrated.
