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Chemical Compound Review:

AG-D-29843 3-(2-hydroxyethyl)-1- [(2R,4S,5R)-4-hydroxy...

Synonyms: SureCN2056583, AC1L2XTJ, CTK4A7348, 3-HE-dU, 111447-33-7, ...

Bhanot, O.S. et al., Zhang, W. et al.

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Disease relevance of Uridine, 2'-deoxy-3-(2-hydroxyethyl)-

The 3-HE-dU lesion blocked DNA replication by the Klenow fragment of Escherichia coli polymerase I (Kf Pol I) and bacteriophage T7 polymerase (T7 Pol) 3' to 3-HE-dU and after incorporating a nucleotide opposite 3-HE-dU [1].

High impact information on Uridine, 2'-deoxy-3-(2-hydroxyethyl)-

The significance of formation of 3-HE-dU in DNA was investigated by in vitro DNA replication of 3-HE-dU [1].
Ethylene oxide, a direct-acting mutagen and carcinogen, produces 3-hydroxyethyldeoxyuridine (3-HE-dU) after initial alkylation at N3 of dC, followed by rapid hydrolytic deamination [1].
Substitution of Kf Pol I (exo-) and T7 Pol (exo-), polymerases lacking 3'-->5' exonuclease proofreading activity, for Kf Pol I and T7 Pol, respectively, facilitated DNA synthesis past 3-HE-dU [1].
It was found that 3-(2-hydroxyethyl)-2'-deoxycytidine is unstable in aqueous solution and undergoes an autoinduced hydrolysis to 3-(2-hydroxyethyl)-2'-deoxyuridine [2].

References

The role of 3-hydroxyethyldeoxyuridine in mutagenesis by ethylene oxide. Bhanot, O.S., Singh, U.S., Solomon, J.J. J. Biol. Chem. (1994) [Pubmed]
Synthesis of 3,N4-etheno, 3,N4-ethano, and 3-(2-hydroxyethyl) derivatives of 2'-deoxycytidine and their incorporation into oligomeric DNA. Zhang, W., Rieger, R., Iden, C., Johnson, F. Chem. Res. Toxicol. (1995) [Pubmed]

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