当前位置: X-MOL 学术J. Org. Chem. › 论文详情
Our official English website, www.x-mol.net, welcomes your feedback! (Note: you will need to create a separate account there.)
Conformational Selection in Anion Recognition: cGMP-Selective Binding by a Naphthalimide-Functionalized Amido-Amine Macrocycle.
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2019-05-22 00:00:00 , DOI: 10.1021/acs.joc.9b00947
Aleksandr S Oshchepkov 1, 2 , Tatiana A Shumilova 1 , Mario Zerson 1 , Robert Magerle 1 , Victor N Khrustalev 2, 3 , Evgeny A Kataev 1
Affiliation  

Amido-amine macrocycles with two and four naphthalimide dyes were designed to bind nucleoside monophosphates and oligonucleotides in an aqueous buffered solution. Anion-templated synthesis was used to direct the macrocyclization reaction to the [2+2] product, while high dilution conditions favored the formation of the [4+4] macrocycle with an unprecedented geometry, as revealed from the X-ray analysis. The [2+2] product was found to exhibit a remarkable binding strength and fluorescence response for cyclic guanosine monophosphate (cGMP) in an aqueous solution. To our knowledge, this is the first synthetic receptor for cGMP, which also demonstrates a high preference to bind guanine-rich sequences accomplished by a strong fluorescence quenching. The receptor conformation is very sensitive to the guest structure in an aqueous solution, thus modeling the adaptive behavior of proteins. The study of synthetic systems with a detectable conformational equilibrium represents a great potential for understanding highly specific and tightly regulated interactions in biological systems.

中文翻译:

阴离子识别中的构象选择:萘二甲酰亚胺官能化的酰胺胺大环化合物对cGMP的选择性结合。

设计具有两种和四种萘二甲酰亚胺染料的酰胺基胺大环化合物,以在缓冲水溶液中结合核苷单磷酸酯和寡核苷酸。X射线分析显示,采用阴离子模板合成法将大环化反应引导至[2 + 2]产物,而高稀释条件则有利于形成具有空前几何形状的[4 + 4]大环。发现[2 + 2]产物对水溶液中的环状鸟苷单磷酸酯(cGMP)表现出显着的结合强度和荧光响应。据我们所知,这是cGMP的第一个合成受体,它也显示出强烈的偏好结合通过强荧光猝灭实现的富含鸟嘌呤的序列。受体构象对水溶液中的客体结构非常敏感,从而模拟蛋白质的适应性行为。具有可检测的构象平衡的合成系统的研究代表了理解生物系统中高度特异性和严格调控的相互作用的巨大潜力。
更新日期:2019-05-22
down
wechat
bug