School of Chemical Engineering, University of Birmingham, Edgbaston, Birmingham B15 2TT, U.K.
School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210093, P. R. China.
J Org Chem. 2020 Jul 2;85(13):8330-8338. doi: 10.1021/acs.joc.0c00173. Epub 2020 Jun 17.
Sialic acid recognition remains an interesting and challenging target in molecular receptor design. Herein, we report a series of benzoboroxole-based receptors in which cationic hydrogen-bond donors have been introduced and shown to promote multipoint sialic acid recognition. One striking feature revealed by these receptors is that the carboxylate sialic acid residue is the primary binding determinant for recognition by benzoboroxole, in which the presence of charge-reinforced hydrogen bonds results in enhanced selectivity for sialic acid over other carbohydrates and a 4.5-fold increase in affinity. These findings open up wide possibilities for benzoboroxole-based receptors use in life science research, biotechnology, and diagnostics.
唾液酸识别仍然是分子受体设计中一个有趣且具有挑战性的目标。在此，我们报告了一系列基于苯并硼唑的受体，其中引入了阳离子氢键供体，并证明其可促进唾液酸的多点识别。这些受体揭示的一个显著特征是，羧酸盐唾液酸残基是苯并硼唑识别的主要结合决定因素，其中电荷增强氢键的存在导致对唾液酸的选择性增强，对其他碳水化合物的选择性提高了 4.5 倍，亲和力也提高了 4.5 倍。这些发现为苯并硼唑基受体在生命科学研究、生物技术和诊断中的应用开辟了广阔的可能性。
