Sugar binding polymers showing high anomeric and epimeric discrimination obtained by noncovalent molecular imprinting.
Sugar binding polymers showing high anomeric and epimeric discrimination obtained by noncovalent molecular imprinting.
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通过非共价分子印迹获得的糖结合聚合物表现出高度异头和差向异构区分度。
作者：
A. Mayes;L. Andersson;K. Mosbach
在乙二醇二甲基丙烯酸酯-甲基丙烯酸共聚物中的糖化合物的非共价分子印迹产生含有高度选择性糖结合位点的材料。一系列聚合物的研究表明，所得的聚合物印迹具有高度的异头和差向异构体的选择性，有利于原来的打印分子。在HPLC分析中，使用对硝基苯基-α-D-半乳糖苷印迹的聚合物可以以接近基线的分辨率分离相同化合物的α和β端基异构体。使用对硝基苯基-β-D-半乳糖苷印迹的聚合物显示出类似的结果，但如预期的那样，β端基异构体保留更长时间。对密切相关的糖进行异头异构体区分也是可能的，分离的程度取决于与打印分子的结构相似性。类似地，用对硝基苯基-α-L-岩藻糖苷印迹的聚合物可以以基线分辨率分离对硝基苯基-L-岩藻糖苷的α/β混合物。使用放射性配体置换分析，使用辛基-α-D-葡糖苷印迹的聚合物显示出与甲基-α-D-葡糖苷结合的亲和力比β-端基异构体高40倍。差向异构体的选择性甚至更令人印象深刻：甲基-α-D-甘露糖苷和甲基-α-D-半乳糖苷的亲和力分别比甲基-α-D-葡糖苷低130倍和240倍。结果进行了讨论，这些聚合物在分离和分析中的可能用途。
Noncovalent molecular imprinting of sugar compounds in ethylene glycol dimethacrylate-methacrylic acid copolymers yielded materials containing highly selective sugar binding sites. Investigation of a range of polymers demonstrated that the resulting polymer imprints have a high degree of both anomeric and epimeric selectivity favoring the original print molecule. In HPLC assays, a polymer imprinted using p-nitrophenyl-alpha-D-galactoside could separate the alpha and beta anomers of the same compound with near baseline resolution. A polymer imprinted using p-nitrophenyl-beta-D-galactoside showed similar results but with the beta anomers retained longer as expected. Anomeric discrimination of closely related sugars was also possible, with the degree of separation depending on the structural resemblance to the print molecule. Similarly, a polymer imprinted with p-nitrophenyl-alpha-L-fucoside could separate alpha/beta mixtures of p-nitrophenyl-L-fucoside with baseline resolution. Using radioligand displacement assays a polymer imprinted using octyl-alpha-D-glucoside was shown to bind methyl-alpha-D-glucoside with a 40-fold higher affinity than that for the beta-anomer. The epimeric selectivity was even more impressive: methyl-alpha-D-mannoside and methyl-alpha-D-galactoside had 130- and 240-fold lower affinity, respectively, than methyl-alpha-D-glucoside. The results are discussed in relation to possible uses of such polymers in separation and analysis.