Charge-Assisted Chalcogen Bonds: CSD and DFT Analyses and Biological Implication in Glucosidase Inhibitors
Charge-Assisted Chalcogen Bonds: CSD and DFT Analyses and Biological Implication in Glucosidase Inhibitors
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DOI：
10.1002/chem.201905498
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发表时间：
2020-03-19
影响因子：
4.3
通讯作者：
Resnati, Giuseppe
中科院分区：
文献类型：
--
作者：
Galmes, Bartomeu;Juan-Bals, Aida;Resnati, Giuseppe
本研究报告了结合剑桥结构数据库和理论DFT研究的电荷辅助的硫键涉及到的硫、硒和碲离子。最近，IUPAC将硫键定义为一个分子实体中与硫原子相关的亲电区域与另一个或相同分子实体中的亲核区域之间的净吸引相互作用。二价硫原子通常有两个西格玛空穴，形成两个chb；采用跷跷板排列的四价碳也是如此。在磺胺、硒鎓和碲鎓盐中，硫原子形成三个共价键，三个sigma空穴位于这些键的对面，在这些空穴和反离子之间可以形成多达三个电荷辅助的ChBs。这些硫原子周围的共价键排列与三价烟原原子相似，并转化为类似的非共价相互作用模式。我们已经在各种含硫离子的葡萄糖苷酶抑制剂中发现并研究了这种类型的电荷辅助硫键，例如salacinol和kotalanol。
This study reports a combined Cambridge Structural Database and theoretical DFT study of charge assisted chalcogen bonds involving sulfonium, selenonium, and telluronium cations. The chalcogen bond has been recently defined by IUPAC as the net attractive interaction between an electrophilic region associated with a chalcogen atom in a molecular entity and a nucleophilic region in another, or the same, molecular entity. Divalent chalcogen atoms typically have up to two sigma-holes and forms up to two ChBs; the same holds for tetravalent chalcogens which adopt a seesaw arrangement. In sulfonium, selenonium, and telluronium salts chalcogen atoms form three covalent bonds, three sigma-holes are located opposite to these bonds, and up to three charge assisted ChBs can be formed between these holes and the counterions. The covalent bond arrangement around these chalcogen atoms is similar to trivalent pnictogen atoms and translates into a similar pattern of noncovalent interactions. We have found and studied this type of charge-assisted chalcogen bonds in various sulfonium ion-containing inhibitors of glucosidase, for example, salacinol and kotalanol.