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2,5-Anhydro-2,5-imino-D-mannitol (CAS 59920-31-9)

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Alternate Names:
2,5-Dideoxy-2,5-imino-D-mannitol
Application:
2,5-Anhydro-2,5-imino-D-mannitol is a modified pyrrolidine
CAS Number:
59920-31-9
Molecular Weight:
163.17
Molecular Formula:
C6H13NO4
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data.

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2,5-Anhydro-2,5-imino-D-mannitol is a chemical compound that has gained significance in scientific research due to its role as an effective inhibitor of various glycosidase enzymes. Its mechanism of action involves mimicking the transition state of natural substrates, thereby competitively inhibiting the enzymatic activity involved in carbohydrate processing pathways. Specifically, this compound has been extensively studied for its inhibitory effects on enzymes such as α-glucosidase and α-mannosidase, crucial players in glycan metabolism and protein glycosylation processes. By interfering with these enzymatic activities, 2,5-Anhydro-2,5-imino-D-mannitol offers insights into the biochemical pathways underlying carbohydrate metabolism and glycan-mediated cellular functions. Furthermore, its structural resemblance to natural substrates enables researchers to probe the specificity and kinetics of glycosidase enzymes, facilitating a deeper understanding of their roles in health and disease. Beyond enzymology, 2,5-Anhydro-2,5-imino-D-mannitol has been employed in chemical biology studies to explain the molecular mechanisms governing glycan recognition, cell-cell interactions, and signaling processes. Through rigorous experimentation and interdisciplinary collaborations, researchers continue to harness the unique properties of 2,5-Anhydro-2,5-imino-D-mannitol to advance our understanding of glycan-mediated biology and pave the way for innovative approaches in drug discovery and biomolecular engineering.


2,5-Anhydro-2,5-imino-D-mannitol (CAS 59920-31-9) References

  1. Novel, lipophilic derivatives of 2,5-dideoxy-2,5-imino-D-mannitol (DMDP) are powerful beta-glucosidase inhibitors.  |  Wrodnigg, TM., et al. 2001. Bioorg Med Chem Lett. 11: 1063-4. PMID: 11327590
  2. Probing the aglycon binding site of a beta-glucosidase: a collection of C-1-modified 2,5-dideoxy-2,5-imino-D-mannitol derivatives and their structure-activity relationships as competitive inhibitors.  |  Wrodnigg, TM., et al. 2004. Bioorg Med Chem. 12: 3485-95. PMID: 15186833
  3. Fine tuning of beta-glucosidase inhibitory activity in the 2,5-dideoxy-2,5-imino-D-mannitol (DMDP) system.  |  Wrodnigg, TM., et al. 2006. Carbohydr Res. 341: 1717-22. PMID: 16616905
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  7. Rare Sugars: Recent Advances and Their Potential Role in Sustainable Crop Protection.  |  Mijailovic, N., et al. 2021. Molecules. 26: PMID: 33808719
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Ordering Information

Product NameCatalog #UNITPriceQtyFAVORITES

2,5-Anhydro-2,5-imino-D-mannitol, 1 mg

sc-220803
1 mg
$223.00

2,5-Anhydro-2,5-imino-D-mannitol, 10 mg

sc-220803A
10 mg
$2237.00

2,5-Anhydro-2,5-imino-D-mannitol, 100 mg

sc-220803B
100 mg
$9384.00

2,5-Anhydro-2,5-imino-D-mannitol, 1 g

sc-220803C
1 g
$15300.00

2,5-Anhydro-2,5-imino-D-mannitol, 5 g

sc-220803D
5 g
$41106.00