62812-42-4

Usage

Uses

Used in Pharmaceutical Industry:
.beta.-D-Glucopyranosiduronic acid, phenyl 1-thio-, methyl ester, triacetate is used as a synthetic intermediate for the production of L-ascorbic acid (vitamin C, A786990). .beta.-D-Glucopyranosiduronic acid, phenyl 1-thio-, methyl ester, triacetate plays a crucial role in the synthesis process, enabling the creation of an essential nutrient that is vital for various biological functions and overall health.
Used in Chemical Industry:
In the chemical industry, .beta.-D-Glucopyranosiduronic acid, phenyl 1-thio-, methyl ester, triacetate can be utilized as a building block for the development of other complex molecules and compounds. Its unique structure and functional groups make it a valuable component in the synthesis of various chemical products, potentially leading to new applications and advancements in the field.

InChI:InChI=1/C19H22O9S/c1-10(20)25-14-15(26-11(2)21)17(27-12(3)22)19(28-16(14)18(23)24-4)29-13-8-6-5-7-9-13/h5-9,14-17,19H,1-4H3/t14-,15-,16+,17-,19-/m0/s1

Upstream product

• 4551-15-9 phenylthiotrimethylsilane 
• 7355-18-2 (2S,3S,4S,5R,6S)-3,4,5,6-Tetraacetoxy-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 108-98-5 thiophenol 
• 21085-72-3 1-bromo-2,3,4-tri-O-acetyl-α-D-glucuronic acid methyl ester 
• 3082-96-0 methyl 1,2,3,4-tetra-O-acetyl-α,β-D-glucopyranosyluronate 
• 3111-52-2 potassium thiophenolate 

Downstream Products

• 26399-82-6 phenyl 1-thio-β-D-glucopyranosiduronic acid 
• 20736-12-3 3-O-acetyl-6-O-(methyl 2',3',4'-tri-O-acetyl-β-D-glucopyranosyluronate)morphine 
• 2784-73-8 6-monoacetylmorphine 
• 561-27-3 Diamorphine 
• 1350467-71-8 methyl (phenyl 2,3-di-O-acetyl-4-deoxy-1-thio-α-L-threo-hex-4-enopyranosid)uronate 
• 1350467-68-3 phenyl 4-deoxy-1-thio-α-L-threo-hex-4-enopyranosiduronic acid 
• 174193-97-6 (2S,3S,4S,5R,6R)-3,4,5-Triacetoxy-6-((2S,3R,4S,5S,6R)-2-acetoxy-3,5-bis-benzoyloxy-6-benzoyloxymethyl-tetrahydro-pyran-4-yloxy)-tetrahydro-pyran-2-carboxylic acid methyl ester 

Relevant academic research and scientific papers

Glycoside cleavage by a new mechanism in unsaturated glucuronyl hydrolases

Unsaturated glucuronyl hydrolases (UGLs) from GH family 88 of the CAZy classification system cleave a terminal unsaturated sugar from the oligosaccharide products released by extracellular bacterial polysaccharide lyases. This pathway, which is involved in extracellular bacterial infection, has no equivalent in mammals. A novel mechanism for UGL has previously been proposed in which the enzyme catalyzes hydration of a vinyl ether group in the substrate, with subsequent rearrangements resulting in glycosidic bond cleavage. However, clear evidence for this mechanism has been lacking. In this study, analysis of the products of UGL-catalyzed reactions in water, deuterium oxide, and dilute methanol in water, in conjunction with the demonstration that UGL rapidly cleaves thioglycosides and glycosides of inverted anomeric configuration (substrates that are resistant to hydrolysis by classical glycosidases), provides strong support for this new mechanism. A hydration-initiated process is further supported by the observed UGL-catalyzed hydration of a C-glycoside substrate analogue. Finally, the observation of a small β-secondary kinetic isotope effect suggests a transition state with oxocarbenium ion character, in which the hydrogen at carbon 4 adopts an axial geometry. Taken together, these observations validate the novel vinyl ether hydration mechanism and are inconsistent with either inverting or retaining direct hydrolase mechanisms at carbon 1.

Synthesis and glycosaminoglycan priming activity of three disaccharides related to the linkage region tetrasaccharide of proteoglycans

To test if disaccharides might serve as primers of oligosaccharide synthesis in animal cells, we synthesized 2-naphthyl O-(β-D-galactopyranosyl)-(1 -> 4)-β-D--xylopyranoside, 2-naphthyl O-(β-D-galactopyranosyl)-1 -> 3)-β-D-galactopyranoside, and 2-naphthyl O-(β-D-glucopyranosyluronic acid)-(1 -> 3)-β-D-galactopyranoside.These three disaccharides are related to subunits of the linkage tetrasaccharide of heparan sulfate and chondroitin sulfate chains in animal cell proteoglycans.The disaccharides were synthesized with coupling efficiencies of 40-70percent using thioglycosides or by activating the monosaccharides with trichloroacetimidate.The structures of these compounds were confirmed by 1H NMR, 13C NMR and elemental analysis.The ability of these disaccharides to prime glycosaminoglycan chains was examined in a Chinese hamster ovary cell mutant, p gsA 745, which lacks xylosyltransferase.The missing enzyme renders the cells dependent on exogenous primers for making glycosaminoglycan chains. 2-Naphthyl O-(β-D-galactopyranosyl)-(1 -> 3)-β-D-galactopyranoside and 2-naphthyl O-(β-D-glucopyranosyluronic acid)-(1 -> 3)-β-D-galactopyranoside did not stimulate glycosaminoglycan synthesis, but 2-naphthyl O-(β-D-galactopyranosyl)-(1 -> 4)-β-D-xylopyranoside at high concentration primed chains.The peracetylated derivative (2-naphthyl O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1 -> 4)-2,3-di-O-acetyl-β-D-xylopyranoside) primed chains at lower concentration (100 μM), suggesting that cells took up the compound and removed the acetyl groups apparently in the compartment where glycosaminoglycan synthesis occurs. - Keywords: Proteoglycans; Glycosaminoglycan priming activity