335202-84-1Relevant academic research and scientific papers
Synthesis and characterization of nucleosides and oligonucleotides bearing adducts of butadiene epoxides on adenine N6 and guanine N2
Nechev, Lubomir V.,Zhang, Mingzhu,Tsarouhtsis, Dimitrios,Tamura, Pamela J.,Wilkinson, Amanda S.,Harris, Constance M.,Harris, Thomas M.
, p. 379 - 388 (2001)
Butadiene is a major industrial chemical whose genotoxic effects are attributed to the reaction of its oxidized metabolites, butadiene monoepoxide (BDO) and butadiene diepoxide (BDO2), with DNA. Nucleosides and oligonucleotides containing regio- and stereochemically specific adducts of BDO and the BDO2-related compound, butene 3,4-diol 1,2-epoxide (BDE), on guanine [(2R)- and (2S)-N2-(1-hydroxy-3-buten-2-yl) and (2R,3R)- and (2S,3S)-N2-(2,3,4-trihydroxybut-1-yl), respectively] and on adenine [(2R)- and (2S)-N6-(1-hydroxy-3-buten-2-yl) and (2R,3R)- and (2S,3S)-N6-(2,3,4-trihydroxybut-1-yl), respectively] have been prepared by nonbiomimetic routes. For guanine adducts, 2-fluoro-O6-(trimethylsilylethyl)-2′-deoxyinosine was treated with (2R)- and (2S)-2-amino-3-buten-1-ol to give the BDO adducts and with (2R,3R)- and (2S,3S)-1-amino-2,3,4-butanetriol to produce the BDE adducts; the adducted oligonucleotides were prepared from 11-mer oligonucleotides containing the halopurine. Adenine adducts were prepared in a similar fashion using 6-chloropurine 2′-deoxyriboside as the reactive purine component.
