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2-Deoxy-2-fluoro-D-galactose (CAS 51146-53-3)

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CAS Number:
51146-53-3
Molecular Weight:
182.15
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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2-Deoxy-2-fluoro-D-galactose is a monosaccharide analog that is utilized in chemical and biological research for its ability to mimic natural sugars while possessing altered chemical properties due to the fluorine substitution. It is of interest in the study of glycosylation processes, where it is used to probe the specificity and mechanism of glycosyltransferases, enzymes that facilitate the transfer of sugar moieties to various substrates. This sugar analog is also employed in the exploration of metabolic pathways, specifically to understand how such structural changes affect the incorporation and utilization of sugars in organisms. In addition, 2-Deoxy-2-fluoro-D-galactose is used in the synthesis of glycoconjugates for research into cell surface interactions and signaling, as the modified sugar can influence binding affinity and biological activity.


2-Deoxy-2-fluoro-D-galactose (CAS 51146-53-3) References

  1. Synthesis of deoxyfluoro sugars from carbohydrate precursors.  |  Dax, K., et al. 2000. Carbohydr Res. 327: 47-86. PMID: 10968676
  2. Enzymatic synthesis of UDP-(3-deoxy-3-fluoro)-D-galactose and UDP-(2-deoxy-2-fluoro)-D-galactose and substrate activity with UDP-galactopyranose mutase.  |  Barlow, JN. and Blanchard, JS. 2000. Carbohydr Res. 328: 473-80. PMID: 11093703
  3. Differential mechanism-based labeling and unequivocal activity assignment of the two active sites of intestinal lactase/phlorizin hydrolase.  |  Arribas, JC., et al. 2000. Eur J Biochem. 267: 6996-7005. PMID: 11106409
  4. Inhibition of protein N-glycosylation by 2-deoxy-2-fluoro-D-galactose.  |  Gross, V., et al. 1992. Biochem J. 285 (Pt 3): 821-6. PMID: 1497619
  5. 2-Deoxy-2-fluoro-D-galactose protein N-glycosylation.  |  Loch, N., et al. 1991. FEBS Lett. 294: 217-20. PMID: 1756864
  6. Novel method for chase analysis of oligosaccharide metabolic error caused by xenobiotics.  |  Kato, T., et al. 2010. Anal Biochem. 405: 103-8. PMID: 20570645
  7. Metabolism and actions of 2-deoxy-2-fluoro-D-galactose in vivo.  |  Grün, BR., et al. 1990. Eur J Biochem. 190: 11-9. PMID: 2114284
  8. In vivo metabolism and UTP-depleting action of 2-deoxy-2-fluoro-D-galactose.  |  Grün, BR., et al. 1990. Adv Enzyme Regul. 30: 231-42. PMID: 2403033
  9. Structural basis for binding of fluorinated glucose and galactose to Trametes multicolor pyranose 2-oxidase variants with improved galactose conversion.  |  Tan, TC., et al. 2014. PLoS One. 9: e86736. PMID: 24466218
  10. Mechanism-based inhibitors of glycosidases: design and applications.  |  Kallemeijn, WW., et al. 2014. Adv Carbohydr Chem Biochem. 71: 297-338. PMID: 25480507
  11. Multi-level glyco-engineering techniques to generate IgG with defined Fc-glycans.  |  Dekkers, G., et al. 2016. Sci Rep. 6: 36964. PMID: 27872474
  12. Conserved FcγR- glycan discriminates between fucosylated and afucosylated IgG in humans and mice.  |  Dekkers, G., et al. 2018. Mol Immunol. 94: 54-60. PMID: 29268168
  13. Synthetic strategies for fluorination of carbohydrates.  |  Uhrig, ML., et al. 2019. Org Biomol Chem. 17: 5173-5189. PMID: 31017598
  14. A 19F NMR study of 2-deoxy-2-fluoro-D-galactose in mice.  |  Kanazawa, Y., et al. 1988. Chem Pharm Bull (Tokyo). 36: 4213-6. PMID: 3245998
  15. The use of deoxyfluoro-D-galactopyranoses in a study of yeast galactokinase specificity.  |  Thomas, P., et al. 1974. Biochem J. 139: 661-4. PMID: 4369372

Ordering Information

Product NameCatalog #UNITPriceQtyFAVORITES

2-Deoxy-2-fluoro-D-galactose, 10 mg

sc-220724A
10 mg
$235.00

2-Deoxy-2-fluoro-D-galactose, 25 mg

sc-220724
25 mg
$380.00

2-Deoxy-2-fluoro-D-galactose, 50 mg

sc-220724B
50 mg
$568.00

2-Deoxy-2-fluoro-D-galactose, 100 mg

sc-220724C
100 mg
$1057.00

2-Deoxy-2-fluoro-D-galactose, 250 mg

sc-220724F
250 mg
$1546.00

2-Deoxy-2-fluoro-D-galactose, 1 g

sc-220724E
1 g
$6811.00