51. Synthesis of G- N 2 -(CH 2 ) 3 - N 2 -G Trimethylene DNA interstrand cross-links.
- Author
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Gruppi F, Salyard TL, and Rizzo CJ
- Abstract
The synthesis of G- N
2 -(CH2 )3 -G trimethylene DNA interstrand cross-links (ICLs) in a 5'-CG-3' and 5'-GC-3' sequence from oligodeoxynucleotides containing N2 -G trimethylene DNA interstrand cross-links (ICLs) in a 5'-CG-3' and 5'-GC-3' sequence from oligodeoxynucleotides containing N2 -(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 of N2 -(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 N2 -(3-aminopropyl)-2'-deoxyguanosine and 2-fluoro- O6 -(trimethylsilylethyl)inosine containing oligodeoxynucleotides.- Published
- 2014
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