The effect of the structural differences in the reducing terminus of sugars on the binding affinity of carbohydrates and proteins analyzed using photoaffinity labeling.

The effect of the structural differences in the reducing terminus of sugars on the binding affinity of carbohydrates and proteins analyzed using photoaffinity labeling.
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使用光亲和标记分析糖还原末端的结构差异对碳水化合物和蛋白质结合亲和力的影响。

DOI:
10.1016/j.bmc.2010.11.067
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发表时间:
2011
期刊:
Bioorg Med. Chem.
影响因子:
--
通讯作者:
Akiyo Sakushima
Akiyo Sakushima
中科院分区:
--
文献类型:
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作者:
Isao Ohtsuka;Yutaka Sadakane;Mari Higuchi;Noriyasu Hada;Junko Hada;Nobuko Kakiuchi;Akiyo Sakushima

文献摘要

相似文献

由于碳水化合物和蛋白质结合的亲和力如此之低,它们相互作用的性质尚不清楚。与二氮丙啶基团的光亲和标记是有用的,阐明碳水化合物在这些结合过程中的作用。然而,当根据该常规方法合成碳水化合物探针时,糖的还原末端被打开以提供无环结构。因为更好地阐明碳水化合物-蛋白质相互作用需要一个闭环碳水化合物除了光反应基团,我们合成了新的分子工具。碳水化合物配体的合成分三步(糖基化与烯丙醇,脱保护,臭氧分解)。通过光亲和标记获得糖配体的特异性结合蛋白。其中还原糖是封闭的闭环型碳水化合物配体比开环型糖更强地与凝集素结合。使用AFM观察碳水化合物与蛋白质的结合。
Because carbohydrates and proteins bind with such low affinity, the nature of their interactions is not clear. Photoaffinity labeling with diazirin groups is useful for elucidating the roles of carbohydrates in these binding processes. However, when carbohydrate probes are synthesized according to this conventional method, the reducing terminus of the sugar is opened to provide an acyclic structure. Because greater elucidation of carbohydrate–protein interactions requires a closed-ring carbohydrate in addition to the photoreactive group, we synthesized new molecular tools. The carbohydrate ligands were synthesized in three steps (glycosylation with allyl alcohol, deprotection, and ozonolysis). Specific binding proteins for carbohydrate ligands were obtained by photoaffinity labeling. Closed ring-type carbohydrate ligands, in which the reducing sugar is closed, bound to lectins more strongly than open ring-type sugars. Carbohydrate to protein binding was observed using AFM.