Mechanochemistry of nucleosides, nucleotides and related materials.

Mechanochemistry of nucleosides, nucleotides and related materials.
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DOI:
10.3762/bjoc.14.81
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发表时间:
2018
影响因子:
2.7
通讯作者:
Liang Y
Liang Y
中科院分区:
化学4区
文献类型:
--
作者:
Eguaogie O;Vyle JS;Conlon PF;Gîlea MA;Liang Y

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应用机械力诱导共价键的形成和断裂是有机化学中一个迅速发展的领域,在减少或消除溶剂使用量、提高反应速度以及在制备在溶液相条件下无法获得的产品方面具有特殊的价值。机械力化学最近也在材料化学和原料药配方方面引起了关注,在这些过程中,非共价相互作用的重排产生了功能产品。然而,这一点几乎是从19世纪末核酸科学开始就知道的,当时Miescher利用研磨通过选择性变性紧密结合的蛋白质来促进DNA的解聚。尽管球磨在氨基酸化学中得到了广泛的应用,但在制备规模上涉及核苷或核苷酸底物的机械力化学转化的报道还很有限。提供了对这些反应的调查,其中大多数使用了混合器球磨机,并显示了对研磨容器内存在液体的几乎普遍要求。特别是,带电核苷酸底物的机械化学能在效率方面提供相当大的好处(将总处理时间从几周减少到几个小时),并最大限度地减少暴露在水条件下,从而获得以前难以捉摸的材料。在没有大量溶剂和加热的情况下,副反应可以减少或消除。还将概述机械力化学(特别是球磨)对通过研磨分离来自原子核的生物活性物质的主要贡献。最后将介绍利用机械力化学技术实现核酸与相关材料的非共价缔合过程:特别是固溶体、共晶、多晶型转变、碳纳米管溶解和包合物的形成。
The application of mechanical force to induce the formation and cleavage of covalent bonds is a rapidly developing field within organic chemistry which has particular value in reducing or eliminating solvent usage, enhancing reaction rates and also in enabling the preparation of products which are otherwise inaccessible under solution-phase conditions. Mechanochemistry has also found recent attention in materials chemistry and API formulation during which rearrangement of non-covalent interactions give rise to functional products. However, this has been known to nucleic acids science almost since its inception in the late nineteenth century when Miescher exploited grinding to facilitate disaggregation of DNA from tightly bound proteins through selective denaturation of the latter. Despite the wide application of ball milling to amino acid chemistry, there have been limited reports of mechanochemical transformations involving nucleoside or nucleotide substrates on preparative scales. A survey of these reactions is provided, the majority of which have used a mixer ball mill and display an almost universal requirement for liquid to be present within the grinding vessel. Mechanochemistry of charged nucleotide substrates, in particular, provides considerable benefits both in terms of efficiency (reducing total processing times from weeks to hours) and by minimising exposure to aqueous conditions, access to previously elusive materials. In the absence of large quantities of solvent and heating, side-reactions can be reduced or eliminated. The central contribution of mechanochemistry (and specifically, ball milling) to the isolation of biologically active materials derived from nuclei by grinding will also be outlined. Finally non-covalent associative processes involving nucleic acids and related materials using mechanochemistry will be described: specifically, solid solutions, cocrystals, polymorph transitions, carbon nanotube dissolution and inclusion complex formation.
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