Synthesis and Glycan?Protein Interaction Studies of Se-Sialosides by 77Se NMR
Synthesis and Glycan?Protein Interaction Studies of Se-Sialosides by 77Se NMR
复制标题
77Se NMR 合成 Se-Sialoside 及其聚糖与蛋白质相互作用研究
DOI：
10.1021/acs.orglett.9b02303
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发表时间：
2019
期刊：
影响因子：
5.2
通讯作者：
Ando Hiromune
中科院分区：
文献类型：
--
作者：
Suzuki Tatsuya;Hayashi Chieka;Komura Naoko;Tamai Rie;Uzawa Jun;Ogawa Junya;Tanaka Hide-Nori;Imamura Akihiro;Ishida Hideharu;Kiso Makoto;Yamaguchi Yoshiki;Ando Hiromune
为了扩大硒-碳水化合物作为糖的多功能模拟物的潜力，本文中我们讨论了具有高度挑战性和生物学意义的唾液酸硒-糖苷（Se-唾液酸苷）的合成。原位生成的α-唾液酸硒酸根阴离子与亲电试剂反应生成单一立体异构体的α-Se-唾液酸苷。ASe-唾液酸糖苷依次与硒结合，产生三硒代唾液酸糖苷。该分子被用作77 Se核磁共振活性手柄来研究聚糖与蛋白质的相互作用，揭示了唾液酸结合蛋白的不同结合谱。
To expand the potential ofSe-carbohydrates for multifunctional mimicry of sugars, herein we addressed the synthesis of the highly challenging and biologically significantSe-glycosides of sialic acid (Se-sialosides). An α-sialyl selenolate anion generated in situ smoothly reacted with electrophiles to give α-Se-sialosides as single stereoisomers. ASe-sialoside was sequentially incorporated with selenium, producing a triseleno-sialoside. This molecule was used as a77Se NMR-active handle for studying glycan–protein interaction, revealing different binding profiles of sialic acid binding proteins.