103531-01-7

Basic information

• Product Name: β-D-glucopyranosyl-(1->4)-α-D-glucopyranosyl fluoride
• Synonyms: β-D-glucopyranosyl-(1->4)-α-D-glucopyranosyl fluoride
• CAS NO: 103531-01-7
• Molecular Weight: 344.291
• Mol File: 103531-01-7.mol

Chemical Properties

• CAS DataBase Reference: β-D-glucopyranosyl-(1->4)-α-D-glucopyranosyl fluoride(CAS DataBase Reference)
• NIST Chemistry Reference: β-D-glucopyranosyl-(1->4)-α-D-glucopyranosyl fluoride(103531-01-7)
• EPA Substance Registry System: β-D-glucopyranosyl-(1->4)-α-D-glucopyranosyl fluoride(103531-01-7)

Safety Data

• Hazardous Substances Data: 103531-01-7(Hazardous Substances Data)

Upstream product

• 3616-19-1 1',2',3',6',2,3,4,6-octa-O-acetyl-β-D-lactose 
• 14227-57-7 O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1<*>4)-2,3,6-tri-O-acetyl-α-D-glucopyranosyl fluoride 
• 440-02-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl-(1->4)-2,3,6-tri-O-acetyl-α-D-glucopyranosyl fluoride 
• 18464-08-9 2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-D-glucopyranose 
• 22352-19-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranosyl acetate 
• 3616-19-1 1,2,3,6,2',3',4',6'-octa-O-acetylmaltose 
• 3616-19-1 lactose octaacetate 

Downstream Products

• 116458-01-6 2,3,6-Tri-O-(dideutero-phenylmethyl)-4-O-<2,3,4,6-tetra-O-(dideutero-phenylmethyl)-β-D-galactopyranosyl>-α-D-glucopyranosyl fluoride 
• 107715-16-2 2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranosyl fluoride 
• 109785-20-8 O-(β-D-galactopyranosyl)-(1→4)-(β-D-glucopyranosyl)-(1→1)-(2S, 3R, 4E)-2-aminooctadec-4-ene-1,3-diol 
• 100817-30-9 maltosyl(α1->6)α-cyclodextrin 
• 9004-34-6 cellulose 
• 106927-48-4 4-nitrophenyl β-D-glucopyranosyl-(1→4)-β-D-glucopyranosyl-(1→4)-β-D-glucopyranoside 

Relevant articles and documents

SYNTHESIS OF GLYCOSYL FLUORIDES

The present invention relates to a method for producing a glycosyl fluoride of interest, the method comprising providing an internalized exogenous precursor and a genetically modified cell, wherein one or more glycosylation reactions can be performed on the exogenous precursor in the genetically modified cell, the genetically modified cell comprising one or more nucleic acid sequences encoding one or more glycosyltransferase enzymes. The present invention further relates to a compound of the following formula: 2b.

Aqueous Glycosylation of Unprotected Sucrose Employing Glycosyl Fluorides in the Presence of Calcium Ion and Trimethylamine

We report a synthetic glycosylation reaction between sucrosyl acceptors and glycosyl fluoride donors to yield the derived trisaccharides. This reaction proceeds at room temperature in an aqueous solvent mixture. Calcium salts and a tertiary amine base promote the reaction with high site-selectivity for either the 3′-position or 1′-position of the fructofuranoside unit. Because nonenzymatic aqueous oligosaccharide syntheses are underdeveloped, mechanistic studies were carried out in order to identify the origin of the selectivity, which we hypothesized was related to the structure of the hydroxyl group array in sucrose. The solution conformation of various monodeoxysucrose analogs revealed the co-operative nature of the hydroxyl groups in mediating both this aqueous glycosyl bond-forming reaction and the site-selectivity at the same time.

Synthesis of fluorinated maltose derivatives for monitoring protein interaction by 19F NMR

A novel reporter system, which is applicable to the 19F NMR investigation of protein interactions, is presented. This approach uses 2-F-labeled maltose as a spy ligand to indirectly probe protein-ligand or protein-protein interactions of proteins fused or tagged to the maltose-binding protein (MBP). The key feature is the simultaneous NMR observation of both 19F NMR signals of gluco/ manno-type-2-F-maltose-isomers; one isomer (α-gluco-type) binds to MBP and senses the protein interaction, and the nonbinding isomers (β-gluco- and/or α/β-manno-type) are utilized as internal references. Moreover, this reporter system was used for relative affinity studies of fluorinated and nonfluorinated carbohydrates to the maltose-binding protein, which were found to be in perfect agreement with published X-ray data. The results of the NMR competition experiments together with the established correlation between 19F chemical shift data and molecular interaction patterns, suggest valuable applications for studies of protein-ligand interaction interfaces.

Facile synthesis of acetylated glycosyl fluorides derived from di- and tri-saccharides

Peracetylated α-glycopyranosyl flourides of di- and tri-saccharides are obtained in good yields by treatment of the corresponding peracetylated di- and tri-saccharides with pyridinium poly(hydrogen fluoride).The interglycosidic bonds are not cleaved by the reagent.

Alkylation of Glycosyl Fluorides

A direct alkylation of unprotected glycosyl fluorides under mild basic conditions without affecting the anomeric group is reported.Thus peralkylated glycosyl fluorides, applied in Lewis acid catalyzed glycosylations, are now effectively available from the

FORMATION OF 6-O-α-MALTOSYLCYCLOMALTO-OLIGOSACCHARIDES FROM α-MALTOSYL FLUORIDE AND CYCLOMALTO-OLIGOSACCHARIDES BY PULLULANASE

Branched cyclomalto-oligosaccharides are formed when pullulanase from Bacillus acidopullulyticus is incubated with α-maltosyl fluoride (α-G2F) as substrate in the presence of cyclomalto-oligosaccharides as acceptor.It was shown by enzymic and chemical methods that the structures of these branched cyclomaltooligosaccharides are 6-O-α-maltosylcyclomalt-ohexaose (G2-cG6), 6,6'-di-O-α-maltosylcyclomaltohexaose , 6-O-α-maltosylcyclomaltoheptaose (G2-cG7), 6,6'-di-O-α-maltosylcyclomaltoheptaose , and 6,6',6''-tri-O-α-maltosylcyclomaltoheptaose .The optimal conditions for formation of G2-cG6 were studied.About 12 mM G2-cG6 was produced when pullulanase (2.8 U/mL) was incubated with 40 mM α-G2F as substrate and 90 mM cyclomaltohexaose (cG6) as acceptor for 1 h at 60 deg C.The yield of G2-cG6, the main transfer-product, was twenty times that by the condensation of cG6 with α-maltose in the presence of pullulanase.