title: Synthesis of G-N2-(CH2)3-N2-G Trimethylene DNA interstrand cross-links.
abstract: The synthesis of G-N2-(CH2)3-N2-G trimethylene DNA interstrand cross-links (ICLs) in a 5'-CG-3' and 5'-GC-3' sequence from oligodeoxynucleotides containingN2-(3-aminopropyl)-2'-deoxyguanosine and 2-fluoro-O6-(trimethylsilylethyl)inosine is presented. Automated solid-phase DNA synthesis was used for unmodified bases and modified nucleotides were incorporated via their corresponding phosphoramidite reagent by a manual coupling protocol. The preparation of the phosphoramidite reagents for incorporation ofN2-(3-aminopropyl)-2'-deoxyguanosine is reported. The high-purity trimethylene DNA interstrand cross-link product is obtained through a nucleophilic aromatic substitution reaction between theN2-(3-aminopropyl)-2'-deoxyguanosine and 2-fluoro-O6-(trimethylsilylethyl)inosine containing oligodeoxynucleotides.
authors.affiliation: Departments of Chemistry and Biochemistry, Center for Molecular Toxicology, Vanderbilt-Ingram Cancer Center, Vanderbilt University, Nashville, Tennessee.
authors.forename: Francesca
authors.initials: F
authors.lastname: Gruppi
authors.affiliation: Departments of Chemistry and Biochemistry, Center for Molecular Toxicology, Vanderbilt-Ingram Cancer Center, Vanderbilt University, Nashville, Tennessee.
authors.forename: Tracy L Johnson
authors.initials: TL
authors.lastname: Salyard
authors.affiliation: Departments of Chemistry and Biochemistry, Center for Molecular Toxicology, Vanderbilt-Ingram Cancer Center, Vanderbilt University, Nashville, Tennessee.
authors.forename: Carmelo J
authors.initials: CJ
authors.lastname: Rizzo
keywords: DNA; N2-(3-aminopropyl)-2′-deoxyguanosine; interstrand cross-links