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N-Acetyl-D-mannosamine (CAS 7772-94-3)

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Alternate Names:
2-acetamido-2-deoxy-D-mannopyranose
Application:
N-Acetyl-D-mannosamine is an essential precursor of N-acetylneuraminic acid (NeuAc)
CAS Number:
7772-94-3
Purity:
≥97%
Molecular Weight:
221.21
Molecular Formula:
C8H15NO6
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data.

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N-Acetyl-D-mannosamine, a precursor in the sialic acid biosynthesis pathway, plays a pivotal role in glycobiology research and glycosylation studies. Upon uptake into cells, it undergoes enzymatic modification to form N-acetylneuraminic acid (Neu5Ac), a key component of glycoproteins, glycolipids, and polysaccharides. This chemical serves as a substrate for various glycosyltransferases and sialyltransferases, which catalyze the transfer of sialic acid residues onto glycan structures. Researchers utilize N-Acetyl-D-mannosamine in cell culture experiments to modulate cellular sialylation levels and investigate its impact on cell adhesion, migration, and signaling processes. Furthermore, it serves as a precursor for metabolic labeling strategies, such as metabolic glycan labeling and chemoenzymatic glycan engineering, enabling the incorporation of bioorthogonal functional groups into glycans for site-specific labeling and visualization of glycoproteins. Additionally, N-Acetyl-D-mannosamine derivatives are employed in the synthesis of sialic acid analogs and glycan mimetics for studying sialic acid recognition by lectins and pathogens. Through its versatile applications in glycobiology, N-Acetyl-D-mannosamine facilitates the elucidation of glycan-mediated molecular mechanisms and the development of novel tools for glycoscience research.


N-Acetyl-D-mannosamine (CAS 7772-94-3) References

  1. Uptake of N-acetyl-D-mannosamine: an essential intermediate in polysialic acid biosynthesis by Escherichia coli K92.  |  Revilla-Nuin, B., et al. 1999. FEBS Lett. 449: 183-6. PMID: 10338128
  2. Transport of N-acetyl-D-mannosamine and N-acetyl-D-glucosamine in Escherichia coli K1: effect on capsular polysialic acid production.  |  Revilla-Nuin, B., et al. 2002. FEBS Lett. 511: 97-101. PMID: 11821056
  3. Enzymatic phosphorylation of N-acetyl-D-mannosamine.  |  GHOSH, S. and ROSEMAN, S. 1961. Proc Natl Acad Sci U S A. 47: 955-8. PMID: 13704957
  4. Chronic administration of N-acetyl-D-mannosamine improves age-associated impairment of long-term potentiation in the senescence-accelerated mouse.  |  Taniguchi, S., et al. 2015. Neurosci Lett. 598: 41-6. PMID: 25962821
  5. Vibrational Signatures of Isomeric Lithiated N-acetyl-D-hexosamines by Gas-Phase Infrared Multiple-Photon Dissociation (IRMPD) Spectroscopy.  |  Tan, Y., et al. 2017. J Am Soc Mass Spectrom. 28: 539-550. PMID: 28050874
  6. Reactivation of hyperglycemia-induced hypocretin (HCRT) gene silencing by N-acetyl-d-mannosamine in the orexin neurons derived from human iPS cells.  |  Hayakawa, K., et al. 2017. Epigenetics. 12: 764-778. PMID: 28762874
  7. Supplementation With the Sialic Acid Precursor N-Acetyl-D-Mannosamine Breaks the Link Between Obesity and Hypertension.  |  Peng, J., et al. 2019. Circulation. 140: 2005-2018. PMID: 31597453
  8. Kinetic characterization of N-acetyl-D-glucosamine kinase from rat liver and kidney.  |  Allen, MB. and Walker, DG. 1980. Biochem J. 185: 577-82. PMID: 6248026
  9. N-acetyl-D-neuraminic acid synthesis in Escherichia coli K1 occurs through condensation of N-acetyl-D-mannosamine and pyruvate.  |  Rodríguez-Aparicio, LB., et al. 1995. Biochem J. 308 (Pt 2): 501-5. PMID: 7772033
  10. Regulation of capsular polysialic acid biosynthesis by N-acetyl-D-mannosamine, an intermediate of sialic acid metabolism.  |  Revilla-Nuin, B., et al. 1998. FEBS Lett. 426: 191-5. PMID: 9599006

Ordering Information

Product NameCatalog #UNITPriceQtyFAVORITES

N-Acetyl-D-mannosamine, 1 g

sc-221981
1 g
$20.00

N-Acetyl-D-mannosamine, 5 g

sc-221981A
5 g
$40.00

N-Acetyl-D-mannosamine, 100 g

sc-221981B
100 g
$714.00

N-Acetyl-D-mannosamine, 1 kg

sc-221981C
1 kg
$4080.00