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4-Deoxy-4-fluoro-D-mannose (CAS 87764-47-4)

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Application:
4-Deoxy-4-fluoro-D-mannose is shown to interfere with the glycosylation of viral G-protein
CAS Number:
87764-47-4
Molecular Weight:
182.1
Molecular Formula:
C6H11FO5
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data.

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4-Deoxy-4-fluoro-D-mannose is a synthetic derivative of D-mannose that has garnered attention in biochemical and chemical biology research. Its unique fluorinated structure makes it a valuable tool for investigating the role of carbohydrates in various biological processes. One of the key mechanisms of action of this compound lies in its ability to interfere with glycosylation pathways. By replacing the hydroxyl group of mannose with a fluorine atom at the C-4 position, 4-Deoxy-4-fluoro-D-mannose alters the chemical and physical properties of glycans, affecting their recognition by glycan-binding proteins and enzymes involved in glycosylation. In research applications, this compound has been utilized to explain the functions of specific glycan structures in cellular adhesion, signaling, and immune response. Additionally, 4-Deoxy-4-fluoro-D-mannose derivatives have been employed as molecular probes for imaging studies, enabling the visualization and tracking of glycan-mediated processes in living systems. Furthermore, this compound serves as a valuable substrate for enzymatic and chemical synthesis of fluorinated carbohydrates, facilitating the development of novel glycoconjugates and glycomimetics with potential applications in drug delivery, diagnostics, and materials science. Overall, 4-Deoxy-4-fluoro-D-mannose represents a versatile tool for exploring the roles of carbohydrates in biological systems and holds promise for various research endeavors in glycobiology and chemical biology.


4-Deoxy-4-fluoro-D-mannose (CAS 87764-47-4) References

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  2. The role of C-4-substituted mannose analogues in protein glycosylation. Effect of the guanosine diphosphate esters of 4-deoxy-4-fluoro-D-mannose and 4-deoxy-D-mannose on lipid-linked oligosaccharide assembly.  |  McDowell, W., et al. 1987. Biochem J. 248: 523-31. PMID: 2449168
  3. Specificity of GDP-Man:dolichyl-phosphate mannosyltransferase for the guanosine diphosphate esters of mannose analogues containing deoxy and deoxyfluoro substituents.  |  McDowell, W. and Schwarz, RT. 1989. FEBS Lett. 243: 413-6. PMID: 2917659
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  8. Mechanism of inhibition of protein glycosylation by the antiviral sugar analogue 2-deoxy-2-fluoro-D-mannose: inhibition of synthesis of man(GlcNAc)2-PP-Dol by the guanosine diphosphate ester.  |  McDowell, W., et al. 1985. Biochemistry. 24: 8145-52. PMID: 4092061
  9. Metabolism of 3-deoxy-3-fluoro-D-mannose and 4-deoxy-4-fluoro-D-mannose by Saccharomyces cerevisiae S288C.  |  Grier, TJ. and Rasmussen, JR. 1983. Biochem J. 209: 677-85. PMID: 6347179
  10. 4-Deoxy-4-fluoro-D-mannose inhibits the glycosylation of the G protein of vesicular stomatitis virus.  |  Grier, TJ. and Rasmussen, JR. 1984. J Biol Chem. 259: 1027-30. PMID: 6693373

Ordering Information

Product NameCatalog #UNITPriceQtyFAVORITES

4-Deoxy-4-fluoro-D-mannose, 5 mg

sc-220936
5 mg
$380.00