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3-O-Methyl-N-acetyl-D-glucosamine (CAS 94825-74-8)

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Alternate Names:
3-O-methyl-GlcNAc; 2-(acetylamino)-2-deoxy-3-O-methyl-D-glucose
Application:
3-O-Methyl-N-acetyl-D-glucosamine is an inhibitor of N-acetylglucosamine kinase and N-acetylmannosamine kinase
CAS Number:
94825-74-8
Purity:
≥95%
Molecular Weight:
235.20
Molecular Formula:
C9H17NO6
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-O-Methyl-N-acetyl-D-glucosamine (3-OMe-GlcNAc) is an analog of N-acetyl-D-glucosamine that may act to inhibit GlcNAc kinase (N-acetylglucosamine kinase Ki = 17muM) and GLCNE (N-acetylmannosamine kinase Ki = 80muM). Research has shown that this compound does not inhibit glucokinase activity and is therefore thought to be useful for accurate assay of glucokinase activity in pancreatic islets and liver tissues.


3-O-Methyl-N-acetyl-D-glucosamine (CAS 94825-74-8) References

  1. Inhibition of N-acetylglucosamine kinase and N-acetylmannosamine kinase by 3-O-methyl-N-acetyl-D-glucosamine in vitro.  |  Zeitler, R., et al. 1992. Eur J Biochem. 204: 1165-8. PMID: 1312935
  2. Tacrolimus suppresses glucose-induced insulin release from pancreatic islets by reducing glucokinase activity.  |  Radu, RG., et al. 2005. Am J Physiol Endocrinol Metab. 288: E365-71. PMID: 15479952
  3. Decline in glucokinase activity in the arcuate nucleus of streptozotocin-induced diabetic rats.  |  Nishio, T., et al. 2006. Biol Pharm Bull. 29: 216-9. PMID: 16462021
  4. Glucokinase and glucokinase regulatory proteins are functionally coexpressed before birth in the rat brain.  |  Roncero, I., et al. 2009. J Neuroendocrinol. 21: 973-81. PMID: 19807849
  5. Synthesis of N-acetyl Glucosamine Analogs as Inhibitors for Hyaluronan Biosynthesis.  |  Wasonga, G., et al. 2013. J Carbohydr Chem. 32: 392-409. PMID: 27099411
  6. Insecticidal activities of constituents of Litsea cubeba fruit extracts effective against the maize weevil (Coleoptera: Curculionidae).  |  Zhang, HJ., et al. 2017. J Insect Sci. 17: PMID: 29117378
  7. Inhibition of the Hexosamine Biosynthetic Pathway by targeting PGM3 causes breast cancer growth arrest and apoptosis.  |  Ricciardiello, F., et al. 2018. Cell Death Dis. 9: 377. PMID: 29515119
  8. Developmental regulation of Wnt signaling by Nagk and the UDP-GlcNAc salvage pathway.  |  Neitzel, LR., et al. 2019. Mech Dev. 156: 20-31. PMID: 30904594
  9. The Hexosamine Biosynthesis Pathway: Regulation and Function.  |  Paneque, A., et al. 2023. Genes (Basel). 14: PMID: 37107691
  10. Utility of 3-O-methyl-N-acetyl-D-glucosamine, an N-acetylglucosamine kinase inhibitor, for accurate assay of glucokinase in pancreatic islets and liver.  |  Miwa, I., et al. Enzyme Protein. 48: 135-42. PMID: 8589800
  11. Potentiation of glucose-induced insulin secretion by fagomine, a pseudo-sugar isolated from mulberry leaves.  |  Taniguchi, S., et al. 1998. Horm Metab Res. 30: 679-83. PMID: 9918385

Ordering Information

Product NameCatalog #UNITPriceQtyFAVORITES

3-O-Methyl-N-acetyl-D-glucosamine, 1 mg

sc-202886A
1 mg
$102.00

3-O-Methyl-N-acetyl-D-glucosamine, 5 mg

sc-202886
5 mg
$245.00

3-O-Methyl-N-acetyl-D-glucosamine, 10 mg

sc-202886B
10 mg
$388.00

Whether this inhibitor can penetrate cell membrane?

Asked by: Orenda
Thank you for your question. Please contact technical service at (800)-457-3801 or email scbt@scbt.com
Answered by: BlakeJ
Date published: 2022-11-17
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Rated 5 out of 5 by from Miwa I; et alMiwa I; et al. (PubMed ID: 8589800) determined that 3-O-Methyl-N-acetyl-D-glucosamine significantly suppresses glucose phosphorylation by N-acetylglucosamine kinase in rat liver extracts. -SCBT Publication Review
Date published: 2015-04-03
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3-O-Methyl-N-acetyl-D-glucosamine is rated 5.0 out of 5 by 1.
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