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2-Acetamido-2-deoxy-D-galactono-1,4-lactone (CAS 28876-38-2)

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Alternate Names:
2-(Acetylamino)-2-deoxy-D-galactonic Acid γ-Lactone;
Application:
2-Acetamido-2-deoxy-D-galactono-1,4-lactone is an N-acetylglucosaminidase inhibitor
CAS Number:
28876-38-2
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-galactono-1,4-lactone, a derivative of D-galactose, holds significant importance in carbohydrate chemistry research and glycobiology studies. Its unique structure and reactivity make it a valuable tool in the synthesis of complex carbohydrates and glycoconjugates. The mechanism of action involves its ability to undergo ring-opening reactions under mild basic conditions, revealing the reactive hydroxyl group at the C-1 position of the sugar moiety. This hydroxyl group serves as a key site for glycosylation reactions, where it can form glycosidic bonds with acceptor molecules, leading to the synthesis of diverse glycoconjugates. Additionally, the presence of an acetamido group at the C-2 position enhances the stability and selectivity of glycosylation reactions. Researchers utilize 2-Acetamido-2-deoxy-D-galactono-1,4-lactone as a crucial intermediate in the preparation of biologically relevant carbohydrate structures, including glycolipids, glycoproteins, and glycosaminoglycans. Moreover, this compound serves as a valuable probe in elucidating carbohydrate-protein interactions, cell surface recognition processes, and carbohydrate-mediated signaling pathways. Its synthetic accessibility and ability to introduce specific functional groups enable researchers to tailor carbohydrate structures with precise stereochemistry and regioselectivity, advancing our understanding of carbohydrate biology and facilitating the development of novel materials for various research applications in chemistry, biochemistry, and biotechnology.


2-Acetamido-2-deoxy-D-galactono-1,4-lactone (CAS 28876-38-2) References

  1. The inhibitory activities of 2-acetamido-2,3-dideoxy-D-hex-2-enonolactones on 2-acetamido-2-deoxy-beta-D-glucosidase.  |  Pokorny, M., et al. 1975. Carbohydr Res. 43: 345-54. PMID: 1238169
  2. Inhibition of glycosidases by aldonolactones of corresponding configuration. 2. Inhibitors of beta-N-acetylglucosaminidase.  |  FINDLAY, J., et al. 1958. Biochem J. 69: 467-76. PMID: 13560392
  3. Studies on glucosaminidase. 5. Kidney N-acetyl-beta-glucosaminidase and N-acetyl-beta-galactosaminidase.  |  WALKER, PG., et al. 1961. Biochem J. 79: 288-94. PMID: 13782742
  4. The oxidation of 2-acetamido-2-deoxyaldoses with aqueous bromine. Two diastereoisomeric 2-acetamido-2,3-dideoxyhex-2-enono-1,4-lactones from 2-acetamido-2-deoxy-D-glucose, -mannose, and -galactose.  |  Pravdić, N. and Fletcher, HG. 1971. Carbohydr Res. 19: 339-52. PMID: 5151898
  5. Dicyclohexylammonium salts for the isolation and characterization of aldonic acids.  |  Zissis, Emmanuel, et al. 1973. Carbohydrate Research. 26.2: 323-333.
  6. 2-Acetamido-2-deoxyaldonolactones from sugar formazans.  |  Zsoldos-Mady, Virag, et al. 1994. Carbohydrate research. 252: 85-95.

Ordering Information

Product NameCatalog #UNITPriceQtyFAVORITES

2-Acetamido-2-deoxy-D-galactono-1,4-lactone, 10 mg

sc-220680
10 mg
$300.00