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Synthesis of oligonucleotides containing an O-G-alkyl-O-G interstrand cross-link
Authors:Christopher J. Wilds  Jason D. Booth  Anne M. Noronha
Affiliation:Department of Chemistry and Biochemistry, Concordia University, 7141 Sherbrooke St. West, Montreal, QC, Canada H4B 1R6
Abstract:A methodology to synthesize oligonucleotides containing an alkyl interstrand cross-link between the two O6 atoms of deoxyguanosine has been developed. This cross-link is designed to serve as a stable structural mimic of the lesion formed in duplex DNA with the bifunctional alkylating agent hepsulfam. The O6-alkyl coupling is performed via a Mitsunobu reaction between a nucleoside and mono-protected 1,7-heptanediol. Solid-phase oligonucleotide synthesis using a nucleoside bis-phosphoramidite allows for the assembly of the cross-linked duplex. Sufficient quantities of this cross-linked duplex were obtained for various structural and biological investigations.
Keywords:Oligonucleotides   Interstrand cross-link   DNA repair   Cancer
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