AAAA-DDDD 四重氢键辅助离子相互作用：水中稳定的双(胍基)/二羧酸异质双链。

AAAA-DDDD Quadruple H-Bond-Assisted Ionic Interactions: Robust Bis(guanidinium)/Dicarboxylate Heteroduplexes in Water.

机构信息

School of Materials Science and Engineering, Center for Supramolecular Chemistry and Catalysis, and Department of Chemistry , Shanghai University , 99 Shang-Da Road , Shanghai 200444 , China.

School of Chemistry, The Australian Centre for Nanomedicine and ARC Centre of Excellence in Convergent Bio-Nano Science and Technology , University of New South Wales , Sydney 2052 , NSW , Australia.

出版信息

J Am Chem Soc. 2019 Dec 26;141(51):20146-20154. doi: 10.1021/jacs.9b09503. Epub 2019 Dec 13.

DOI:10.1021/jacs.9b09503

PMID:31789022

Abstract

The use of geminal di(guanidinium) and acridin-9(10)-one-derived di(carboxylate) derivatives (- and -, respectively) allows stabilization of heterodimers characterized by high binding affinities in water (maximum Δ < -7 kcal mol, > 10 M) as inferred from UV-vis spectroscopic titrations and ITC measurements, therefore rivaling or surpassing the interaction energy between the strongest DNA or RNA triplet pairs. These duplexes are readily accessible and are structurally modifiable, rendering them attractive as building blocks for creating heteroduplex constructs. Incorporating poly(ethylene glycol)-decorated benzyl groups into the dicarboxylate, allows formation of hydrogels in the case of -.

摘要

使用二（胍鎓）和吖啶-9（10）-酮衍生的二（羧酸酯）衍生物（分别为-和-）可以稳定杂二聚体，这些杂二聚体在水中具有高的结合亲和力（最大 Δ < -7 kcal mol， > 10 M），这可以从紫外可见光谱滴定和 ITC 测量中推断出来，因此可以与最强的 DNA 或 RNA 三碱基对之间的相互作用能量相媲美或超过。这些双链体易于获得并且结构可修饰，使其成为构建异源双链体构建体的有吸引力的构建块。将聚（乙二醇）修饰的苄基基团引入二羧酸酯中，在-的情况下允许形成水凝胶。