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首页> 外文期刊>Nucleic Acids Research >OLIGODEOXYNUCLEOSIDE PHOSPHORAMIDATES (P-NH2) - SYNTHESIS AND THERMAL STABILITY OF DUPLEXES WITH DNA AND RNA TARGETS
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OLIGODEOXYNUCLEOSIDE PHOSPHORAMIDATES (P-NH2) - SYNTHESIS AND THERMAL STABILITY OF DUPLEXES WITH DNA AND RNA TARGETS

机译：寡脱氧核苷磷酸酰胺（P-NH2）-具有DNA和RNA靶标的双链体的合成和热稳定性

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Syntheses of non ionic oligodeoxynucleoside phosphoramidates (P-NH2) and mixed phosphoramidate-phosphodiester oligomers were accomplished on automated solid supported DNA synthesizer using both H-phosphonate and phosphoramidite chemistries, in combination with t-butylphenoxyacetyl for N-protection of nucleoside bases, an oxalyl anchored solid support and a final treatment with methanolic ammonia, Thermal stabilities of the hybrids formed between these new analogues and their DNA and RNA complementary strands were determined and compared with those of the corresponding unmodified oligonucleotides, as well as of the phosphorothioate and methylphosphonate derivatives, Dodecathymidines containing P-NH2 links form less stable duplexes with DNA targets, d(C(2)A(12)C(2)) (Delta Tm/modification -1.4 degrees C) and poly dA (Delta Tm/modification -1.1 degrees C) than the corresponding phosphodiester and methylphosphonate analogues, but the hybrids are slightly more stable than the one obtained with phosphorothioate derivative, The destabilization is more pronounced with poly rA as the target (Delta Tm/modification -3 degrees C) and could be compared with that found with the dodecathymidine methylphosphonate. The modification is less destabilizing in an heteropolymer-RNA duplex (Delta Tm/modification -2 degrees C), As expected, the P-NH2 modifications are highly resistant towards the action of various nucleases, It is also demonstrated that an all P-NH2 oligothymidine does not elicit Escherichia coli RNase H hydrolysis of the poly rA target but that the modification may be exploited in chimeric oligonucleotides combining P-NH2 sections with a central phosphodiester section.
机译：非离子型低聚脱氧核苷氨基磷酸酯（P-NH2）和混合的氨基磷酸酯-磷酸二酯低聚物的合成是在自动固相支持的DNA合成仪上完成的，使用的是H-膦酸酯和亚磷酰胺化学试剂，与叔丁基苯氧基乙酰基结合使用以保护N-保护核苷碱基（草酰）。锚固固体支持物并用甲醇氨进行最终处理，确定了这些新类似物及其DNA和RNA互补链之间形成的杂合体的热稳定性，并将其与相应的未修饰寡核苷酸以及硫代磷酸酯和甲基膦酸酯衍生物的热稳定性进行了比较，含有P-NH2链的十二烷嘧啶与DNA靶标d（C（2）A（12）C（2））（Δtm/修饰-1.4摄氏度）和聚dA（Δtm/修饰-1.1摄氏度）形成不稳定的双链体C）比相应的磷酸二酯和甲基膦酸酯类似物，但杂种比获得的杂种稍稳定无论是硫代磷酸酯衍生物，去稳定化都以聚rA为目标（ΔTm /修饰-3摄氏度）更为明显，可以与十二烷基吡啶甲基膦酸酯的去稳定化作用进行比较。所述修饰在杂聚物-RNA双链体中的不稳定程度较小（ΔTm/修饰-2℃），如所预期的，P-NH2修饰对各种核酸酶的作用具有高度抗性，还证明了全部P-NH2寡胸苷不会引发poly rA靶标的大肠杆菌RNase H水解，但可以在结合P-NH2部分和中央磷酸二酯部分的嵌合寡核苷酸中利用该修饰。

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