Synthesis of DNA oligodeoxynucleotides containing site-specific 1,3-butadiene- deoxyadenosine lesions

Susith Wickramaratne, Christopher L. Seiler, Natalia Y. Tretyakova

Research output: Contribution to journalArticlepeer-review

3 Scopus citations


Post-oligomerization synthesis is a useful technique for preparing site-specifically modified DNA oligomers. This approach involves site-specific incorporation of inherently reactive halogenated nucleobases into DNA strands using standard solid-phase synthesis, followed by post-oligomerization nucleophilic aromatic substitution (SNAr) reactions with carcinogen-derived synthons. In these reactions, the inherent reactivities of DNA and carcinogen-derived species are reversed: the modified DNA nucleobase acts as an electrophile, while the carcinogen-derived species acts as a nucleophile. In the present protocol, we describe the use of the post-oligomerization approach to prepare DNA strands containing site- and stereospecific N6-adenine and N1, N6-adenine adducts induced by epoxide metabolites of the known human and animal carcinogen 1,3-butadiene (BD). The resulting oligomers containing site-specific, structurally defined DNA adducts can be used in structural and biological studies to reveal the roles of specific BD adducts in carcinogenesis and mutagenesis.

Original languageEnglish (US)
Pages (from-to)4.61.1-4.61.22
JournalCurrent protocols in nucleic acid chemistry
StatePublished - 2015

Bibliographical note

Publisher Copyright:
© 2015 by John Wiley & Sons, Inc.


  • 1,3-butadiene-induced DNA adducts
  • Adenine
  • Post-oligomerization synthesis
  • Site- and stereospecific oligodeoxynucleotides


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