Boronic acid-modified nucleoside - synthesis and structural characterisation in the solid state.

IF 1.1 4区 生物学 Q4 BIOCHEMISTRY & MOLECULAR BIOLOGY
Tabea Lenz, Marian Hebenbrock
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引用次数: 0

Abstract

The first structure of a boronic acid-modified nucleoside is elucidated by single-crystal X-ray diffraction and compared to its tert-butyldimethylsilyl-protected nucleoside derivative. Further, we present the synthetic access to boronic acid-modified -nucleosides providing alternative reaction conditions to a reported synthesis. Although the sugar pucker of the boronic acid-modified nucleoside differs slightly from other nucleosides, the geometry around the nucleobase shows a high degree of structural similarity to the nucleosides of the natural nucleobases. Inter- as well as intramolecular hydrogen bonds are present involving the boronic acid residue as donor. The interconnection via hydrogen bonds permits the formation of suprastructures in form of linear zigzag chains in the solid state. In conclusion, the structural influence by the boronic acid residue on the overall nucleoside's geometry was only minor which favours its potential use as functionalised thymidine analogue in deoxyoligonucleotides.

硼酸修饰核苷的合成及固态结构表征。
用单晶x射线衍射分析了硼酸修饰核苷的第一个结构,并将其与叔丁基二甲基硅基保护核苷衍生物进行了比较。此外,我们提出了硼酸修饰核苷的合成途径,为报道的合成提供了替代反应条件。虽然硼酸修饰核苷的糖皱与其他核苷略有不同,但核碱基周围的几何形状显示出与天然核碱基核苷的高度结构相似性。以硼酸残基为供体存在分子间和分子内氢键。通过氢键的相互连接允许在固态中形成线性之字形链的上层结构。总之,硼酸残基对整个核苷几何结构的结构影响很小,这有利于其在脱氧寡核苷酸中作为功能化胸苷类似物的潜在用途。
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来源期刊
Nucleosides, Nucleotides & Nucleic Acids
Nucleosides, Nucleotides & Nucleic Acids 生物-生化与分子生物学
CiteScore
2.60
自引率
7.70%
发文量
91
审稿时长
6 months
期刊介绍: Nucleosides, Nucleotides & Nucleic Acids publishes research articles, short notices, and concise, critical reviews of related topics that focus on the chemistry and biology of nucleosides, nucleotides, and nucleic acids. Complete with experimental details, this all-inclusive journal emphasizes the synthesis, biological activities, new and improved synthetic methods, and significant observations related to new compounds.
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