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Methyl 2-Acetamido-2-deoxy-β-D-glucopyranoside (CAS 3946-01-8)

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Alternate Names:
Methyl N-Acetyl-β-D-glucosaminide
CAS Number:
3946-01-8
Molecular Weight:
235.23
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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Methyl 2-Acetamido-2-deoxy-β-D-glucopyranoside, a derivative of N-acetylglucosamine, plays a vital role in glycobiology research, particularly in investigating carbohydrate-protein interactions and glycan biosynthesis. Its mechanism of action involves serving as a glycosyl donor or acceptor in enzymatic and chemical glycosylation reactions. This compound is extensively utilized in the synthesis of complex carbohydrates and glycoconjugates, such as glycoproteins and glycolipids, for studying various biological processes. Researchers often employ Methyl 2-Acetamido-2-deoxy-β-D-glucopyranoside as a precursor in the preparation of glycan derivatives and glycosylated molecules to probe carbohydrate-mediated events like cell adhesion, signaling, and immune response. Moreover, it serves as a valuable tool in developing glycosylation methodologies and chemoenzymatic approaches for site-specific glycosylation of proteins and peptides. Additionally, this compound finds application in glycan array technologies for high-throughput screening of carbohydrate-binding proteins and pathogens, aiding in the discovery of novel carbohydrate-based vaccines. Overall, Methyl 2-Acetamido-2-deoxy-β-D-glucopyranoside is indispensable in advancing our understanding of glycoscience and has broad applications in glycobiology, chemical biology, and biotechnology research.


Methyl 2-Acetamido-2-deoxy-β-D-glucopyranoside (CAS 3946-01-8) References

  1. The separation of methyl ethers of methyl 2-acetamido-2-deoxy-D-glucopyranosides on a strongly basic ion-exchange resin.  |  Allen, AK., et al. 1976. Carbohydr Res. 51: 149-55. PMID: 1009535
  2. Synthesis of 4-deoxy analogues of 2-acetamido-2-deoxy-D-glucose and 2-acetamido-2-deoxy-D-xylose and their effects on glycoconjugate biosynthesis.  |  Berkin, A., et al. 2000. Carbohydr Res. 325: 30-45. PMID: 10741825
  3. Synthesis of 4-deoxy-4-fluoro analogues of 2-acetamido-2-deoxy-D-glucose and 2-acetamido-2-deoxy-D-galactose and their effects on cellular glycosaminoglycan biosynthesis.  |  Berkin, A., et al. 2000. Carbohydr Res. 326: 250-63. PMID: 10890273
  4. Authentic standards for the reductive-cleavage method. The positional isomers of partially methylated and acetylated or benzoylated methyl 2-(acetylmethylamino)-2-deoxy-beta-D-glucopyranoside.  |  Elvebak, LE., et al. 2000. Carbohydr Res. 329: 799-805. PMID: 11125822
  5. Stereoselective synthesis of [13C]methyl 2-[15N]amino-2-deoxy-beta-D-glucopyranoside derivatives.  |  Boulineau, FP. and Wei, A. 2001. Carbohydr Res. 334: 271-9. PMID: 11527528
  6. Synthesis and biological evaluation of a radiolabeled analog of methyl 2-acetamido-2,4-dideoxy-beta-D-xylo-hexopyranoside directed towards influencing cellular glycosaminoglycan biosynthesis.  |  Berkin, A., et al. 2002. Carbohydr Res. 337: 37-44. PMID: 11755910
  7. Concise and efficient synthesis of 2-acetamido-2-deoxy-beta-D-hexopyranosides of diverse aminosugars from 2-acetamido-2-deoxy-beta-D-glucose.  |  Cai, Y., et al. 2009. J Org Chem. 74: 580-9. PMID: 19132941
  8. Efficient synthesis of D-xylo and D-ribo-phytosphingosines from methyl 2-amino-2-deoxy-beta-D-hexopyranosides.  |  Cai, Y., et al. 2009. Carbohydr Res. 344: 2120-6. PMID: 19766990
  9. Amide cis-trans isomerization in aqueous solutions of methyl N-formyl-D-glucosaminides and methyl N-acetyl-D-glucosaminides: chemical equilibria and exchange kinetics.  |  Hu, X., et al. 2010. J Am Chem Soc. 132: 4641-52. PMID: 20225805
  10. Simultaneous determination of glucosamine and glucosamine 4-phosphate in Lipid A with high-performance anion-exchange chromatography (HPAEC).  |  Kiang, J., et al. 1998. Carbohydr Res. 312: 73-6. PMID: 9836452

Ordering Information

Product NameCatalog #UNITPriceQtyFAVORITES

Methyl 2-Acetamido-2-deoxy-β-D-glucopyranoside, 100 mg

sc-221893
100 mg
$180.00