title: Synthesis of G-N2-(CH2)3-N2-G Trimethylene DNA Interstrand Cross-Links.
abstract: The synthesis of G-N(2)-(CH(2))(3)-N(2)-G trimethylene DNA interstrand cross-links (ICLs) in a 5'-CG-3' and 5'-GC-3' sequence from oligodeoxynucleotides containing N(2)-(3-aminopropyl)-2'-deoxyguanosine and 2-fluoro-O(6)-(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 of N(2)-(3-aminopropyl)-2'-deoxyguanosine is reported. The high-purity trimethylene DNA interstrand cross-link product is obtained through a nucleophilic aromatic substitution reaction between the N(2)-(3-aminopropyl)-2'-deoxyguanosine- and 2-fluoro-O(6)-(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.forename: Tracy L
authors.initials: TL
authors.lastname: Johnson Salyard
authors.forename: Carmelo J
authors.initials: CJ
authors.lastname: Rizzo
mesh_terms: D003432:Cross-Linking Reagents / Q000138:chemical synthesis* / Q000737:chemistry*; D009838:Oligodeoxyribonucleotides / Q000138:chemical synthesis* / Q000737:chemistry*
chemical_list: D003432:Cross-Linking Reagents; D009838:Oligodeoxyribonucleotides
keywords: DNA; N2‐(3‐aminopropyl)‐2′‐deoxyguanosine; interstrand cross‐links