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2-Acetamido-2-deoxy-D-glucono-1,5-lactone (CAS 19026-22-3)

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Alternate Names:
N-Acetylglucosamino-1,5-lactone; 2-Acetamido-2-deoxy-D-gluconolactone
Application:
2-Acetamido-2-deoxy-D-glucono-1,5-lactone is inhibits breakdown of products by beta-hexosaminidase
CAS Number:
19026-22-3
Molecular Weight:
219.19
Molecular Formula:
C8H13NO6
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-Acetamido-2-deoxy-D-glucono-1,5-lactone is a significant compound widely employed in biochemical research, particularly in the investigation of carbohydrate chemistry and enzymatic pathways. Its unique structure, resembling the lactone form of gluconic acid, lends itself to diverse applications in elucidating mechanisms of carbohydrate metabolism and glycosylation processes. This chemical serves as a versatile substrate analog, enabling researchers to explore enzymatic activities involved in the synthesis and modification of complex carbohydrates, such as glycosaminoglycans and glycoproteins. One of its primary roles lies in studying glycosyltransferases, enzymes pivotal in glycosylation reactions where sugar moieties are transferred to acceptor molecules. By utilizing 2-Acetamido-2-deoxy-D-glucono-1,5-lactone, scientists can investigate enzyme kinetics, substrate specificities, and regulatory mechanisms governing glycosylation pathways. Moreover, this compound has found applications in structural biology, facilitating the determination of glycan structures through chemical modification and derivatization strategies. Its versatility extends to glycobiology studies, enabling the manipulation of carbohydrate biosynthetic pathways and providing insights into their roles in cellular functions and disease processes. Overall, 2-Acetamido-2-deoxy-D-glucono-1,5-lactone stands as a crucial tool in advancing our understanding of carbohydrate biochemistry and its implications in various biological systems.


2-Acetamido-2-deoxy-D-glucono-1,5-lactone (CAS 19026-22-3) References

  1. Sperm N-acetylglucosaminidase is involved in primary binding to the zona pellucida.  |  Zitta, K., et al. 2006. Mol Hum Reprod. 12: 557-63. PMID: 16829627
  2. Bovine N-acetyl-beta-D-glucosaminidase: affinity purification and characterization of its active site with nitrogen containing analogs of N-acetylglucosamine.  |  Legler, G., et al. 1991. Biochim Biophys Acta. 1080: 89-95. PMID: 1932095
  3. Nanomolar inhibition of human OGA by 2-acetamido-2-deoxy-d-glucono-1,5-lactone semicarbazone derivatives.  |  Kiss, M., et al. 2021. Eur J Med Chem. 223: 113649. PMID: 34186233
  4. 2-Acetamido-2-deoxy-d-glucono-1,5-lactone Sulfonylhydrazones: Synthesis and Evaluation as Inhibitors of Human OGA and HexB Enzymes.  |  Kiss, M., et al. 2022. Int J Mol Sci. 23: PMID: 35162960
  5. The inhibitory activity of 2-acetamido-2-deoxy-D-gluconolactones and their isopropylidene derivatives on 2-acetamido-2-deoxy-beta-D-glucosidase.  |  Pokorny, M., et al. 1974. Carbohydr Res. 37: 321-29. PMID: 4442037
  6. [Enzymatic isomerization of 2-acetamido-2-deoxy-D-glucono-(1,5)-lactone by N-acetyl-beta-D-glucosamindidase].  |  Khorlin, AIa., et al. 1973. Biokhimiia. 38: 1095-7. PMID: 4780969
  7. Stereochemistry of products of hydrolysis of 2-acetamido-2-deoxy- -D-glucosides by boar epididymis 2-acetamido-2-deoxy- -D-glucosidase.  |  Khorlin, AY., et al. 1972. Carbohydr Res. 21: 316-9. PMID: 5065147
  8. On the inhibition of beta-N-acetyl-D-glucosaminidase by 2-acetamido-2-deoxy-D-glucono-(1-5)-lactone.  |  Leaback, DH. 1968. Biochem Biophys Res Commun. 32: 1025-30. PMID: 5750221
  9. Photoaffinity labeling of human lysosomal beta-hexosaminidase B. Identification of Glu-355 at the substrate binding site.  |  Liessem, B., et al. 1995. J Biol Chem. 270: 23693-9. PMID: 7559539

Ordering Information

Product NameCatalog #UNITPriceQtyFAVORITES

2-Acetamido-2-deoxy-D-glucono-1,5-lactone, 25 mg

sc-220684
25 mg
$347.00

2-Acetamido-2-deoxy-D-glucono-1,5-lactone, 250 mg

sc-220684A
250 mg
$4080.00