2713-54-4

Usage

Uses

Used in Biochemistry and Enzymology:
α-D-mannopyranosyl fluoride is used as a competitive inhibitor for glycosidase enzymes to test their activity. This application aids in understanding the enzyme's function and mechanism.
Used in Pharmaceutical Research:
α-D-mannopyranosyl fluoride is used as a potential drug candidate in the development of treatments for diseases such as diabetes and cancer. Its role in understanding glycosylation mechanisms contributes to the discovery of novel therapeutic agents.
Used in Antibiotic Development:
α-D-mannopyranosyl fluoride is used as an inhibitor of bacterial glycosyl hydrolases, making it a potential target for the development of new antibiotics to combat bacterial infections.
Used in the Study of Glycosylation Mechanisms:
α-D-mannopyranosyl fluoride is used to investigate the mechanisms of glycosylation, which is essential for the development of drugs that can modulate these processes for therapeutic purposes.

Upstream product

• 1226-39-7 p-nitrophenyl-β-D-fucopyranoside 
• 35599-02-1 4-nitrophenyl-β-D-mannopyranoside 
• 2106-10-7 1-deoxy-1-fluoro-α-D-glucose 
• 2001-96-9 p-nitrophenyl β-D-xylopyranoside 
• 2492-87-7 4-nitrophenyl-β-D-glucoside 
• 3150-24-1 4-nitrophenyl-β-D-galactopyranoside 
• 171626-64-5 2,4-dinitrophenyl β-D-mannopyranoside 
• 18968-05-3 1,3,4,6-tetra-O-acetyl-β-D-mannopyranose 
• 221252-41-1 1,3,4,6-tetra-O-acetyl-2-O-methanesulfonyl-β-D-mannose 
• 221252-44-4 2-O-methanesulfonyl-β-D-mannose 
• 439-03-2 2-(acetoxymethyl)-6-fluorotetrahydro-2H-pyran-3,4,5-triyl triacetate 

Downstream Products

• 29074-00-8 2,2,2-Trifluoroethyl β-D-glucopyranoside 
• 29074-00-8 2,2,2-Trifluoroethyl α-D-glucopyranoside 
• 3198-49-0 (2R,3R,4S,5S,6R)-2-Ethoxy-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol 
• 3198-49-0 ethyl α-D-glucopyranoside 
• 492-62-6 alpha-D-glucopyranose 
• 97-30-3 methyl-alpha-D-glucopyranoside 
• 492-61-5 β-D-glucose 
• 3482-57-3 p-nitrophenyl-α-D-glucopyranosyl-(1→4)-O-α-D-glucopyranoside 
• 72647-96-2 4-nitrophenyl α-isomaltoside 
• 3150-20-7 4-methoxyphenyl β-D-glucopyranoside 
• 78962-39-7 methyl α-D-mannopyranosyl-(1→6)-α-D-mannopyranoside 

Relevant academic research and scientific papers

β-mannosynthase: Synthesis of β-mannosides with a mutant β-mannosidase

Engineering enzymes: The glutamic acid nucleophile of a retaining β-mannosidase has been replaced with a serine residue to form a β-mannosynthase. When the new enzyme is provided with an α-mannosyl fluoride donor and an appropriate acceptor,β-mannoside linkages are synthesized (see scheme). Remarkably, a-mannosyl fluoride can be generated in situ by providing the mannosynthase with excess fluoride ion.

Glycosynthase with broad substrate specificity-an efficient biocatalyst for the construction of oligosaccharide library

A versatile glycosynthase (TnG-E338A) with strikingly broad substrate scope has been developed from Thermus nonproteolyticus β-glycosidase (TnG) by using site-directed mutagenesis. The practical utility of this biocatalyst has been demonstrated by the facile generation of a small library containing various oligosaccharides and a steroidal glycoside (total 25 compounds) in up to 100 % isolated yield. Moreover, an array of eight gluco-oligosaccharides has been readily synthesized by the enzyme in a one-pot, parallel reaction, which highlights its potential in the combinatorial construction of a carbohydrate library that will assist glycomic and glycotherapeutic research. Significantly, the enzyme provides a means by which glycosynthase technology may be extended to combinatorial chemistry.

Creation of an α-mannosynthase from a broad glycosidase scaffold

α-Mannosides made easy: Mutation of a family-GH31 α-glucosidase that displays plasticity to alterations at the 2-OH position of donor substrates created an efficient α-mannoside-synthesizing biocatalyst. A simple fluoride donor reagent was used for the synthesis of a range of mono-α-mannosylated conjugates using the α-mannosynthase displaying low (unwanted) oligomerization activity. Copyright

Synthesis of 1-[18F]fluorodeoxyglucose: An unexpected rearrangement in the reaction of 2-O-methanesulfonyl-β-D-mannopyranose with [18F]fluoride

2-O-Methanesulfonyl-β-D-mannose was reacted with kryptofix/K2CO3/[18F]fluoride in CH3CN/THF (9:1) at 60°C. Unexpectedly, a mixture of 1α- and 1β-glucopyranosyl [18F]fluoride (4 and 5, respectively) was obtained in 50% radiochemical yield (EOB); 2-[18F]FDG was not detected. Modification of temperature, solvent or pH did not result in the formation of 2-[18F]FDG. Uptake of radioactivity in heart and brain of mice was significantly lower for 4 and 5 than for 2-[18F]FDG, although 5 seems to pass the blood-brain barrier. Uptake in bone was more pronounced for 4 than for 5 and negligible for 2-[18F]FDG.