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首页> 外文期刊>Nucleic Acids Research >Synthesis end properties of RNA analogs - oligoribonucleotide N3 '-> P5 'phosphoramidates
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Synthesis end properties of RNA analogs - oligoribonucleotide N3 '-> P5 'phosphoramidates

机译：RNA类似物-寡核糖核苷酸N3'-> P5'磷酸氨基甲酸酯的合成末端性质

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摘要

The synthesis and characterization of RNA mimetics, uniformly modified oligoribonucleotide N3'-->P5' phosphoramidates containing all four natural bases (uracil, cytosine, adenine and guanine) as well as thymidine and 2,6-diaminopurine, are described, These RNA analogs contain N3'-->P5' phosphoramidate internucleotide linkages which replaced natural RNA O3'-->P5' phosphodiester groups. These oligonucleotides were constructed from novel monomeric units (2'-t-butyldimethylsilyl)-3'-(monomethoxyltrityl)-amino-nucleoside-5'-phos phoramidites, the preparation of which is also presented. Several mixed base 9-13mer oligoribonucleotide phosphoramidates were synthesized with step-wise coupling yields of 96-98%, Thermal denaturation experiments demonstrated that ribo-N3'-->P5' phosphoramidates form stable duplexes with a complementary RNA strand. Thus, the melting temperature (T-m) of a duplex formed by a 13mer ribo-N3'-->P5' phosphoramidate (84 degrees C) was higher than that observed for the isosequential natural RNA oligomer (64.0 degrees C), or for the 2'-deoxy-N3'-->P5' phosphoramidate counterpart (71.7 degrees C). Moreover, substitution of adenine by 2,6-diaminopurine in an oligoribophosphoramidate pentamer resulted in a very significant increase in the duplex melting temperature (similar to 7 degrees C per base substitution). The RNA phosphoramidates also showed similar rates of hydrolysis by both RNase A and RNase T-1 as compared to natural RNA oligomers, The data presented indicate that this class of RNA analogs may be used as structural and functional RNA mimetics.
机译：描述了RNA模拟物，均匀修饰的寡核糖核苷酸N3'-> P5'氨基磷酸酯的合成和表征，该寡核苷酸包含所有四个天然碱基（尿嘧啶，胞嘧啶，腺嘌呤和鸟嘌呤）以及胸苷和2,6-二氨基嘌呤，这些RNA类似物含有N3'-> P5'氨基磷酸酯核苷酸间键，取代了天然RNA O3'-> P5'磷酸二酯基。这些寡核苷酸由新颖的单体单元（2'-叔丁基二甲基甲硅烷基）-3'-（单甲氧基苯甲基）-氨基-核苷-5'-亚磷酰胺构成，其制备也已提出。合成了几种混合碱基的9-13mer寡核糖核苷酸氨基磷酸酯，逐步偶联产率为96-8％。热变性实验表明，核糖-N3'-> P5'氨基磷酸酯与互补的RNA链形成稳定的双链体。因此，由13mer核糖-N3'-> P5'氨基磷酸酯形成的双链体的解链温度（Tm）（84摄氏度）高于等序天然RNA低聚物（64.0摄氏度）或2'-deoxy-N3'-> P5'氨基磷酸酯对应物（71.7摄氏度）。此外，在低聚磷酰胺基戊酸酯五聚体中用2，6-二氨基嘌呤取代腺嘌呤导致双链体熔解温度非常显着提高（类似于每个碱基取代7摄氏度）。与天然RNA寡聚物相比，RNA氨基磷酸酯还显示出类似的被RNase A和RNase T-1水解的速率。提供的数据表明，此类RNA类似物可用作结构和功能的RNA模拟物。

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