G-(CH₂)₃-G三亚甲基DNA链间交联的合成。
Synthesis of G--(CH)--G Trimethylene DNA interstrand cross-links.
作者信息
Gruppi Francesca, Salyard Tracy L Johnson, Rizzo Carmelo J
机构信息
Departments of Chemistry and Biochemistry, Center for Molecular Toxicology, Vanderbilt-Ingram Cancer Center, Vanderbilt University, Nashville, Tennessee.
出版信息
Curr Protoc Nucleic Acid Chem. 2014 Mar 26;5(514):5.14.1-5.14.15. 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.
本文介绍了从含有-(3-氨丙基)-2'-脱氧鸟苷和2-氟-(三甲基硅乙基)肌苷的寡脱氧核苷酸中合成5'-CG-3'和5'-GC-3'序列的G--(CH)--G三亚甲基DNA链间交联(ICLs)。未修饰的碱基采用自动化固相DNA合成，修饰的核苷酸通过相应的亚磷酰胺试剂通过手动偶联方案掺入。报道了用于掺入-(3-氨丙基)-2'-脱氧鸟苷的亚磷酰胺试剂的制备。通过含-(3-氨丙基)-2'-脱氧鸟苷和2-氟-(三甲基硅乙基)肌苷的寡脱氧核苷酸之间的亲核芳香取代反应，获得了高纯度的三亚甲基DNA链间交联产物。
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