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Carmelo Rizzo
Faculty Member
Last active: 1/7/2016

Synthesis of G--(CH)--G Trimethylene DNA interstrand cross-links.

Gruppi F, Salyard TL, Rizzo CJ
Curr Protoc Nucleic Acid Chem. 2014 5 (514): 5.14.1-5.14.15

PMID: 25431636 · PMCID: PMC4242527 · DOI:10.1002/0471142700.nc0514s56

The synthesis of G--(CH)--G trimethylene DNA interstrand cross-links (ICLs) in a 5'-CG-3' and 5'-GC-3' sequence from oligodeoxynucleotides containing -(3-aminopropyl)-2'-deoxyguanosine and 2-fluoro--(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 -(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 -(3-aminopropyl)-2'-deoxyguanosine and 2-fluoro--(trimethylsilylethyl)inosine containing oligodeoxynucleotides.

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