5-Hydroxy-2'-deoxyuridine

• CAT Number: I016938
• CAS Number: 5168-36-5
• Molecular Formula: C9H12N2O6
• Molecular Weight: 244.20
• Purity: ≥95%
• Synonyms: 5-hydroxy-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione
• InChI: InChI=1S/C9H12N2O6/c12-3-6-4(13)1-7(17-6)11-2-5(14)8(15)10-9(11)16/h2,4,6-7,12-14H,1,3H2,(H,10,15,16)/t4-,6+,7+/m0/s1
• InChIKey: UIJSURSVLVISBO-UBKIQSJTSA-N
• SMILES: C1C(C(OC1N2C=C(C(=O)NC2=O)O)CO)O

5-Hydroxy-2′-deoxyuridine (5-OHdU) is a major stable oxidation product of 2′-Deoxycytidine. 5-Hydroxy-2′-deoxyuridine can be incorporated into DNA in vitro by DNA polymerase[1].
To study the specificity of nucleotide incorporation opposite 5-hydroxypyrimidines in template DNA, 18- and 45-member oligodeoxyribonucleotides, containing an internal 2′-deoxy-5-hydroxyuridine (5-OHdU) in two different sequence contexts, were used. Translesion synthesis past 2′-deoxy-5-hydroxyuridine (5-OHdU) in both oligonucleotides occurred, but pauses both opposite, and one nucleotide prior to, the modified base in the template is observed. The specificity of nucleotide incorporation opposite 2′-deoxy-5-hydroxyuridine (5-OHdU) in the template is sequence context dependent. In one sequence context, dA is the principal nucleotide incorporated opposite 2′-deoxy-5-hydroxyuridine (5-OHdU). However in a second sequence context, dC is the predominant base incorporated opposite 2′-deoxy-5-hydroxyuridine (5-OHdU). In that same sequence context, dC is also the predominant nucleotide incorporated opposite 2′-deoxy-5-hydroxyuridine (5-OHdU)[1].

Reference

[1]. Purmal AA, et al. Major oxidative products of cytosine, 5-hydroxycytosine and 5-hydroxyuracil, exhibit sequence context-dependent mispairing in vitro. Nucleic Acids Res. 1994 Jan 11;22(1):72-8.
 [Content Brief]