2-氮杂嘌呤核苷：寡核苷酸的合成、性质和碱基配对。
2-azapurine nucleosides: synthesis, properties, and base pairing of oligonucleotides.
机构信息
Laboratory of Bioorganic Chemistry and Chemical Biology, Center for Nanotechnology, Heisenbergstrasse 11, Münster.
出版信息
Chem Biodivers. 2010 Sep;7(9):2145-90. doi: 10.1002/cbdv.201000162.
This review deals with 2-azapurine (imidazo[4,5-d] [1,2,3]triazine) nucleosides and closely related analogs. Different routes are described to yield the desired target compounds, including a sequence of ring-opening and ring-closure reactions performed on purine nucleosides or direct glycosylation of a 2-azapurine nucleobase with a sugar halide. Further, physical and spectroscopic properties of 2-azapurine nucleosides are discussed, including fluorescence, (13)C-NMR data, single-crystal X-ray analyses, and conformation studies on selected compounds; new biological data are presented. The second part of this review is dedicated to oligonucleotides containing 2-azapurines, including building-block (phosphoramidite) preparation and their use in solid-phase oligonucleotide synthesis. Base-pairing properties of 2-azapurine nucleosides as surrogates of canonical constituents of DNA were evaluated.
这篇综述涉及 2-氮杂嘌呤（咪唑并[4,5-d] [1,2,3]三嗪）核苷及其密切相关的类似物。描述了不同的路线来生成所需的目标化合物，包括在嘌呤核苷上进行开环和闭环反应的序列，或者直接用糖卤化物对 2-氮杂嘌呤碱基进行糖苷化。此外，还讨论了 2-氮杂嘌呤核苷的物理和光谱性质，包括荧光、(13)C-NMR 数据、单晶 X 射线分析和选定化合物的构象研究；呈现了新的生物学数据。这篇综述的第二部分专门介绍了含有 2-氮杂嘌呤的寡核苷酸，包括构建块（亚磷酰胺）的制备及其在固相寡核苷酸合成中的应用。评估了 2-氮杂嘌呤核苷作为 DNA 规范成分替代物的碱基配对性质。
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