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D-Glucal (CAS 13265-84-4)

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Application:
D-Glucal is A building block used in synthesis
CAS Number:
13265-84-4
Molecular Weight:
146.14
Molecular Formula:
C6H10O4
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data.

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D-Glucal, a versatile carbohydrate derivative, holds significant importance in glycobiology research due to its unique structural features and diverse applications in studying carbohydrate chemistry and biology. Its mechanism of action primarily revolves around its role as a precursor molecule in the synthesis of complex carbohydrates and glycoconjugates. Researchers utilize D-Glucal as a building block for the construction of carbohydrate structures with specific stereochemical configurations, facilitating the study of carbohydrate-protein interactions and glycan-mediated processes. Moreover, this compound serves as a substrate for enzymes involved in glycosylation reactions, enabling the investigation of enzymatic mechanisms and kinetics in glycan biosynthesis pathways. Its structural resemblance to natural carbohydrates makes it a valuable tool for studying carbohydrate metabolism, cellular recognition processes, and host-pathogen interactions. Furthermore, D-Glucal finds applications in the synthesis of glycoconjugates and glycomimetics for use in biochemical assays, structural studies, and drug discovery research. Its versatile utility extends to carbohydrate-based materials science, where it contributes to the development of biomaterials, nanocarriers, and glycan arrays for various biomedical and biotechnological applications. Through its diverse research applications, D-Glucal continues to advance our understanding of carbohydrate biology and pave the way for innovative research strategies aimed at unraveling the roles of glycans in biological systems.


D-Glucal (CAS 13265-84-4) References

  1. New stereoselective beta-glycosylation via a vinyl oxirane derived from D-glucal.  |  Bussolo, VD., et al. 2002. Org Lett. 4: 3695-8. PMID: 12375921
  2. Regio- and stereoselectivity of the addition of O-, S-, N-, and C-nucleophiles to the beta vinyl oxirane derived from D-glucal.  |  Di Bussolo, V., et al. 2004. J Org Chem. 69: 8702-8. PMID: 15575746
  3. Reaction on D-glucal by an inverting phosphorylase to synthesize derivatives of 2-deoxy-beta-D-arabino-hexopyranosyl-(1-->4)-D-glucose (2II-deoxycellobiose).  |  Kitaoka, M., et al. 2006. Carbohydr Res. 341: 545-9. PMID: 16430877
  4. Synthesis of sporiolide B from D-glucal.  |  Chen, Q. and Du, Y. 2007. Carbohydr Res. 342: 1405-11. PMID: 17517381
  5. Examining the role of phosphate in glycosyl transfer reactions of Cellulomonas uda cellobiose phosphorylase using D-glucal as donor substrate.  |  Wildberger, P., et al. 2012. Carbohydr Res. 356: 224-32. PMID: 22591555
  6. The non-metabolizable glucose analog D-glucal inhibits aflatoxin biosynthesis and promotes kojic acid production in Aspergillus flavus.  |  Zhang, JD., et al. 2014. BMC Microbiol. 14: 95. PMID: 24742119
  7. Synthesis of pyranobenzopyrans from D-glucal using ionic liquids.  |  Eltayeb, S. and Marzabadi, CH. 2023. Carbohydr Res. 531: 108873. PMID: 37421875
  8. Radical Ring Opening Polymerization of Cyclic Ketene Acetals Derived From d-Glucal.  |  Hardy, C., et al. 2023. ACS Macro Lett. 12: 1443-1449. PMID: 37824416
  9. General acid-base catalysis of alpha-glucan phosphorylases: stereospecific glucosyl transfer from D-glucal is a pyridoxal 5'-phosphate and orthophosphate (arsenate) dependent reaction.  |  Klein, HW., et al. 1982. Biochemistry. 21: 6675-84. PMID: 7159553
  10. Further syntheses employing phosphorylase.  |  Evers, B. and Thiem, J. 1997. Bioorg Med Chem. 5: 857-63. PMID: 9208097

Ordering Information

Product NameCatalog #UNITPriceQtyFAVORITES

D-Glucal, 1 g

sc-221480
1 g
$190.00