寡聚-2-嘧啶酮-2'-脱氧核糖核苷酸和寡聚-2-嘧啶酮-2'-脱氧核苷甲基膦酸酯的固相合成
Solid-phase synthesis of oligo-2-pyrimidinone-2'-deoxyribonucleotides and oligo-2-pyrimidinone-2'-deoxyriboside methylphosphonates.
作者信息
Zhou Y, Ts'o P O
机构信息
Department of Biochemistry, School of Hygiene and Public Health, Johns Hopkins University, Baltimore, MD 21205, USA.
出版信息
Nucleic Acids Res. 1996 Jul 15;24(14):2652-9. doi: 10.1093/nar/24.14.2652.
Abstract
A synthetic method was developed for the synthesis of oligodeoxyribonucleotides and oligodeoxyribonucleoside methylphosphonates comprised exclusively of the fluorescent 2-pyrimidinone base for the first time. The method utilized the solid-phase 2-cyanoethylphosphoramidite and methylphosphonamidite chemistry for internucleotide couplings and a baselabile oxalyl linkage to anchor the oligomers onto the CPG support. Cleavage of the oligomers from the support was effected by a short treatment of the support with 5% ammonium hydroxide in methanol at room temperature, without any degradation of the base-sensitive 2-pyrimidinone residues or the base-sensitive methylphosphonate backbone.
摘要
首次开发了一种合成方法，用于合成仅由荧光2-嘧啶酮碱基组成的寡脱氧核糖核苷酸和寡脱氧核糖核苷甲基膦酸酯。该方法利用固相2-氰基乙基亚磷酰胺和甲基膦酰胺化学进行核苷酸间偶联，并使用碱不稳定的草酰基连接将寡聚物锚定在CPG载体上。通过在室温下用5%氢氧化铵的甲醇溶液对载体进行短时间处理，可将寡聚物从载体上切割下来，而不会使对碱敏感的2-嘧啶酮残基或对碱敏感的甲基膦酸酯主链发生任何降解。
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