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3-Deoxy-D-glycero-D-galacto-2-nonulosonic Acid (CAS 153666-19-4)

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Alternate Names:
Ketodeoxynonulosonic acid
Application:
3-Deoxy-D-glycero-D-galacto-2-nonulosonic Acid is a naturally occuring deaminated sialic acid
CAS Number:
153666-19-4
Purity:
98%
Molecular Weight:
268.22
Molecular Formula:
C9H16O9
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data.

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3-Deoxy-D-glycero-D-galacto-2-nonulosonic Acid, referred to as KDN, is a sialic acid derivative that has interest in glycobiology research. This compound is a key component in the study of glycan structures and their biological functions, as it is found in certain fish eggs and mammalian cells. Researchers leverage 3-Deoxy-D-glycero-D-galacto-2-nonulosonic Acid to explore cell-cell recognition processes, signal transduction, and the roles of sialic acids in the development of neural tissues. Additionally, 3-Deoxy-D-glycero-D-galacto-2-nonulosonic Acid′s similarity to other sialic acids makes it a critical molecule for investigating the specificity and mechanisms of sialyltransferases, enzymes that transfer sialic acid to glycoproteins and glycolipids. Its presence in various biologically active compounds also means that 3-Deoxy-D-glycero-D-galacto-2-nonulosonic Acid is an important target for chemical synthesis, contributing to a deeper understanding of the biochemical pathways and interactions in which sialic acids are involved.


3-Deoxy-D-glycero-D-galacto-2-nonulosonic Acid (CAS 153666-19-4) References

  1. Metabolite fingerprinting in transgenic Nicotiana tabacum altered by the Escherichia coli glutamate dehydrogenase gene.  |  Mungur, R., et al. 2005. J Biomed Biotechnol. 2005: 198-214. PMID: 16046826
  2. Synthesis of the nucleoside analogues of 3-deoxy-D-glycero-D-galacto-2-nonulosonic acid (KDN).  |  Nakamura, M., et al. 1991. Nucleic Acids Symp Ser. 137-9. PMID: 1842057
  3. Catalytic nucleophilic glyoxylation of aldehydes.  |  Steward, KM. and Johnson, JS. 2010. Org Lett. 12: 2864-7. PMID: 20481613
  4. Stereoselective Synthesis of 5-epi-α-Sialosides Related to the Pseudaminic Acid Glycosides. Reassessment of the Stereoselectivity of the 5-Azido-5-deacetamidosialyl Thioglycosides and Use of Triflate as Nucleophile in the Zbiral Deamination of Sialic Acids.  |  Dhakal, B., et al. 2016. J Org Chem. 81: 10617-10630. PMID: 27806203
  5. Identification of a Kdn biosynthesis pathway in the haptophyte Prymnesium parvum suggests widespread sialic acid biosynthesis among microalgae.  |  Wagstaff, BA., et al. 2018. J Biol Chem. 293: 16277-16290. PMID: 30171074
  6. Creation and filtering of a recurrent spectral library of CHO cell metabolites and media components.  |  Telu, KH., et al. 2021. Biotechnol Bioeng. 118: 1491-1510. PMID: 33404064
  7. Small RNAs are modified with N-glycans and displayed on the surface of living cells.  |  Flynn, RA., et al. 2021. Cell. 184: 3109-3124.e22. PMID: 34004145
  8. Oxidative deamination of amino sugars: recent advances.  |  Sarpe, VA. and Crich, D. 1979. Carbohydr Chem. 72: 312-314. PMID: 34290849
  9. Effects of the Probiotic, Lactobacillus delbrueckii subsp. bulgaricus, as a Substitute for Antibiotics on the Gastrointestinal Tract Microbiota and Metabolomics Profile of Female Growing-Finishing Pigs.  |  Mo, J., et al. 2022. Animals (Basel). 12: PMID: 35883325
  10. Untargeted metabolomic profiling of fresh and dried leaf extracts of young and mature Eucalyptus globulus trees indicates differences in the presence of specialized metabolites.  |  Pinto, M., et al. 2022. Front Plant Sci. 13: 986197. PMID: 36452102
  11. Glia-neuron coupling via a bipartite sialylation pathway promotes neural transmission and stress tolerance in Drosophila.  |  Scott, H., et al. 2023. Elife. 12: PMID: 36946697
  12. A novel sialidase capable of cleaving 3-deoxy-D-glycero-D-galacto-2-nonulosonic acid (KDN).  |  Li, YT., et al. 1994. Arch Biochem Biophys. 310: 243-6. PMID: 8161211
  13. Analysis of the N-acetylneuraminic acid and N-glycolylneuraminic acid contents of glycoproteins by high-pH anion-exchange chromatography with pulsed amperometric detection.  |  Rohrer, JS., et al. 1998. Glycobiology. 8: 35-43. PMID: 9451012
  14. Identification of the glycosidically bound sialic acid in mucin glycoproteins that reacts as 'free sialic acid' in the Warren assay.  |  Bhavanandan, VP., et al. 1998. Glycobiology. 8: 1077-86. PMID: 9751794

Ordering Information

Product NameCatalog #UNITPriceQtyFAVORITES

3-Deoxy-D-glycero-D-galacto-2-nonulosonic Acid, 5 mg

sc-220863A
5 mg
$198.00

3-Deoxy-D-glycero-D-galacto-2-nonulosonic Acid, 10 mg

sc-220863
10 mg
$312.00

3-Deoxy-D-glycero-D-galacto-2-nonulosonic Acid, 25 mg

sc-220863B
25 mg
$599.00

3-Deoxy-D-glycero-D-galacto-2-nonulosonic Acid, 50 mg

sc-220863C
50 mg
$895.00

3-Deoxy-D-glycero-D-galacto-2-nonulosonic Acid, 100 mg

sc-220863D
100 mg
$1457.00