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ProductsBack/5-(Hydroxymethyl)-2-deoxycytidine [7226-77-9]
Chemical Structure
Chemical Structure
Chemical Structure

5-(Hydroxymethyl)-2-deoxycytidine [7226-77-9]

Research Use Only
AG-CR1-3532
AdipoGen Life Sciences
Estimated Purity>98%
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Product group Chemicals
Molecular Weight257.2
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Overview

  • Supplier
    AdipoGen Life Sciences
  • Product Name
    5-(Hydroxymethyl)-2-deoxycytidine [7226-77-9]
  • Delivery Days Customer
    10
  • Certification
    Research Use Only
  • Estimated Purity
    >98%
  • Hazard Information
    Non-hazardous
  • Molecular Formula
    C10H15N3O5
  • Molecular Weight
    257.2
  • Scientific Description
    Chemical. CAS: 7226-77-9. Formula: C10H15N3O5. MW: 257.2. Synthetic. Epigenetic base. A modified pyrimidine that is capable of producing interstrand cross-links in double-stranded DNA and has been used to quantify DNA hydroxymethylation levels in biological samples. Enriched in the brain, suggesting a role in epigenetic control of neuronal function. Used in epigenetic research and important for cancer research. Potent HIV-1 reverse transcriptase activity inhibitor. Can be used as building block in nucleoside and nucleotide chemistry. - Epigenetic base. A modified pyrimidine that is capable of producing interstrand cross-links in double-stranded DNA and has been used to quantify DNA hydroxymethylation levels in biological samples. Enriched in the brain, suggesting a role in epigenetic control of neuronal function. Used in epigenetic research and important for cancer research. Potent HIV-1 reverse transcriptase activity inhibitor. Can be used as building block in nucleoside and nucleotide chemistry.
  • SMILES
    O[C@H]1C[C@H](N2C=C(CO)C(N)=NC2=O)O[C@@H]1CO
  • Storage Instruction
    2°C to 8°C,-20°C
  • UNSPSC
    12352200

References

  • Interstrand cross-link formation in duplex and triplex DNA by modified pyrimidines: X. Peng, et al.; JACS 130, 10299 (2008)
  • The nuclear DNA base, 5-hydroxymethylcytosine is present in brain and enriched in Purkinje neurons: S. Kriaucionis & N. Heintz; Science 324, 929 (2009)
  • 5-Modified-2'-dU and 2'-dC as mutagenic anti HIV-1 proliferation agents: synthesis and activity: Y. El Sadafi, et al.; J. Med. Chem. 53, 1534 (2010)
  • Determination of genomic 5-hydroxymethyl-2'-deoxycytidine in human DNA by capillary electrophoresis with laser induced fluorescence: A.M. Krais, et al.; Epigenetics 6, 560 (2011)
  • Detection of oxidation products of 5-methyl-2'-deoxycytidine in Arabidopsis DNA: S. Liu, et al.; PLoS One 8, e84620 (2013)
  • Synthesis of a DNA promoter segment containing all four epigenetic nucleosides: 5-Methyl-, 5-hydroxymethyl-, 5-formyl-, and 5-carboxy-2'-deoxycytidine: A.S. Schroeder, et al.; Angew. Chem. Int. Ed. 53, 315 (2014)
  • Hydroxyl-radical-induced oxidation of 5-methylcytosine in isolated and cellular DNA: G.S. Madugundu, et al.; Nucleic Acids Res. 42, 7450 (2014)
  • CDA directs metabolism of epigenetic nucleosides revealing a therapeutic window in cancer; M. Zauri, et al.; Nature 524, 114 (2015)