5-Hydroxymethyl-dC

For general laboratory use.

Shipping: shipped at ambient temperature

Storage Conditions: store at -20 °C
Short term exposure (up to 1 week cumulative) to ambient temperature possible.

Shelf Life: 24 months after date of delivery

Molecular Formula: C₁₀H₁₅N₃O₅

Molecular Weight: 257.24 g/mol

Exact Mass: 257.10 g/mol

CAS#: 7226-77-9

Purity: ≥ 97 % (HPLC)

Form: solid

Color: white to off-white

Spectroscopic Properties: λ_max 275 nm, ε 7.7 L mmol^-1 cm^-1 (Tris-HCl pH 7.5)

Applications:
Epigenetic therapy^[1,6]
Metabolism of dC substituted at position 5^[2,3,5,7]
Influence on DNA promotor ^[4]

Selected References:
[1] Zauri et al. (2015) CDA directs metabolism of epigenetic nucleosides revealing a therapeutic window in cancer. Nature 524:114.
[2] Guz et al. (2014) Comparison of the absolute level of epigenetic marks 5-methylcytosine, 5-hydroxymethylcytosine, and 5-hydroxymethyluracil between human leukocytes and sperm. Biol. Reprod. 91:55.
[3] Liu et al. (2013) Detection of oxidation products of 5-methyl-2'-deoxycytidine in Arabidopsis DNA. PLoS One 8:e84620.
[4] Schroeder (2014) Synthesis of a DNA promoter segment containing all four epigenetic nucleosides: 5-Methyl-, 5-hydroxymethyl-, 5-formyl-, and 5-carboxy-2'-deoxycytidine. Angew. Chem. Int. Ed. 53:315.
[5] Schiesser et al. (2013) Deamination, oxidation, and C-C bond cleavage reactivity of 5-hydroxymethylcytosine, 5-formylcytosine, and 5-carboxycytosine. J. Am. Chem. Soc. 135 (39):14593.
[6] El Sadafi et al. (2010) 5-Modified-2'-dU and 2'-dC as mutagenic anti HIV-1 proliferation agents: synthesis and activity. J. Med. Chem. 53 (4):1534.
[7] Madugundu et al. (2014) Hydroxyl-radical-induced oxidation of 5-methylcytosine in isolated and cellular DNA. Nucleic Acids Res. 42 (11):7450.