Lectin array is an important tool in the fields of carbohydrate chemistry, glycobiology, and glycomics. Because natural lectins are associated with some apparent disadvantages such as tedious purification and easy loss of activity, artificial materials are applied to overcome such shortages by mimicking and replacing lectins in an artificial lectin array, among which boronate affinity-based materials are very outstanding and widely used. However, complicated synthetic works are often involved to design and create boronate affinity-based lectin-mimics. In this work, a facile and novel method was proposed to establish a virtual lectin array based on boronate affinity-based pH-featured encoding for discrimination of monosaccharides by pattern recognition. The dependence of boronate affinity on environmental pH was selected to encode each monosaccharide for feature generation, and the pH-featured encoding was used to construct the virtual lectin array. On the basis of the virtual array, pattern recognition algorithms were applied for data analysis. Monosaccharides were discriminated by principal component analysis, and the relations in the virtual lectin array were unraveled by cluster analysis. In this proof-of-concept work, without complicated synthesis or preparation, the proposed method was successful in mimicking lectin array and discriminating nine elementary monosaccharides found in nature, and it was also a new way of encoding in expanding the applications of boronate affinity-based materials and methods in the field of biomimetics.
Wenqi Zhao,Meihuan Yao,Huidan Liu,Tingru Du,Zhijun Guo,Binbin Zhang,Yujie Wang,Guangyue Bai
Tailoring of the arylboronic acid structures is essential for developing specific monosaccharide (MS) recognition receptors, in which the designed boronic acid derivative should have an appropriate pKa, a stereostructure matched with the target MS, and an easily detectable method. Herein, we report a novel bis(m-benzylammonium) boronic acid with an ethyl spacer (BTEAB) as the receptor molecule to MS. Owing to its unique lyotropic acidity and intrinsic fluorescence characteristics in aqueous solution, BTEAB provides a new strategy for the design of MS sensors. The cation−π interaction promotes the self-assembly behavior of BTEAB and the lyotropic acidity and fluorescence quenching induced by aggregation. The aggregation behavior of BTEAB was confirmed by Rayleigh light scattering, fluorescence, and 1H NMR, and its lyotropic acidity is quantified by the decrease in its acid dissociation constant pKa. It was found that the esterification of BTEAB with three model MSs (fructose, glucose, and galactose) does not destroy the aggregates, indicating that the lyotropic acidity is an applicable characteristic for regulating the pH value of MS recognition. The affinity of BTEAB with MS and the structures of BTEAB-MS ester were studied mainly by isothermal titration calorimetry (ITC), fluorescence and NMR. The interaction mechanism of BTEAB with different MS was proposed. This work provides new insights into MS recognition under about physiological pH adjusted by diarylboronic acid aggregation.
危险品化学品经营许可证（带存储）