5-(Hydroxymethyl)-2'-deoxycytidine

Article No AG-CR1-3532-M001
Product Type Chemicals & Biochemicals
Research Area Epigenetics
Format Powder
Size 1 mg

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Specifications

CAS No 7226-77-9
MW 257.2
Country Availability DK, EE, FI, IS, LT, LV, NO, SE
Data Sheet Link https://www.adipogen.com/productmanagement/resource/download/type/sheet/id/10977
Description 5-(Hydroxymethyl)-2'-deoxycytidine
Supplier Adipogen Life Sciences
Notes 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.
Molecular Formula C10H15N3O5
Alias Names 5 hmdC; 2'-Deoxy-5-(hydroxymethyl)-cytidine
Purity >98%
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)
Solubility Soluble in DMSO (10mg/ml) or water (5mg/ml).
Storage -20°C
Technical Specifications 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.

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