Mark Nana Kwame Afari, Ninna Heikinmäki, Pasi Virta, Tuomas Lönnberg
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引用次数: 0
摘要
合成了各种单链和发夹型 DNA 及 2´-O-methyl-RNA 寡核苷酸,这些寡核苷酸含有由 O1 和 O2 或 O1 和 O3 合成的单个 (2R,3S)-4-(methoxyamino)butane-1,2,3-triol 残基。在弱酸性条件下,将这些寡核苷酸与典型核碱基的甲酰基甲基衍生物和 2-甲基苯并咪唑的等摩尔混合物进行孵育,结果显示,双螺旋(尤其是 A 型双螺旋)的碱基堆叠非常有利于修饰位点的碱基填充。在 2´-O-methyl-RNA 发夹型寡核苷酸中,(2R,3S)-4-(甲氧基氨基)丁烷-1,2,3-三醇残基与核碱基醛的碱基填充遵循沃森-克里克碱基配对规则,胸腺嘧啶是唯一的例外。在单链寡核苷酸或三螺旋的霍格施泰因链中,碱基填充的产量和选择性都要小得多。
The Impact of Secondary Structure on the Base-Filling of N-Methoxy-1,3-Oxazinane (MOANA) and N-Methoxy-1,3-Oxazolidine Glycol Nucleic Acid (MOGNA) Oligonucleotides.
Various single-stranded and hairpin-forming DNA and 2´-O-methyl-RNA oligonucleotides bearing a single (2R,3S)-4-(methoxyamino)butane-1,2,3-triol residue esterified from either O1 and O2 or O1 and O3 were synthesized. Incubation of these oligonucleotides with equimolar mixtures of formylmethyl derivatives of the canonical nucleobases and 2-methylbenzimidazole under mildly acidic conditions revealed base-filling of the modified site to be strongly favored by base stacking of a double-helix, especially an A-type one. In 2´-O-methyl-RNA hairpin oligonucleotides, base-filling of the (2R,3S)-4-(methoxyamino)butane-1,2,3-triol residue with nucleobase aldehydes followed the rules of Watson-Crick base pairing, thymine being the only exception. In single-stranded oligonucleotides or the Hoogsteen strand of triple helices, both the yield and selectivity of base-filling were much more modest.
期刊介绍:
ChemBioChem (Impact Factor 2018: 2.641) publishes important breakthroughs across all areas at the interface of chemistry and biology, including the fields of chemical biology, bioorganic chemistry, bioinorganic chemistry, synthetic biology, biocatalysis, bionanotechnology, and biomaterials. It is published on behalf of Chemistry Europe, an association of 16 European chemical societies, and supported by the Asian Chemical Editorial Society (ACES).