Determination of protonation states of iminosugar–enzyme complexes using photoinduced electron transfer,Chemical Science

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Determination of protonation states of iminosugar–enzyme complexes using photoinduced electron transfer
Chemical Science ( IF 7.6 ) Pub Date : 2017-09-14 00:00:00 , DOI: 10.1039/c7sc01540b
Bo Wang ₁ , Jacob Ingemar Olsen ₁ , Bo W Laursen ₁ , Jens Christian Navarro Poulsen ₁ , Mikael Bols ₁

Affiliation

A series of N-alkylated analogues of 1-deoxynojirimycin containing a fluorescent 10-chloro-9-anthracene group in the N-alkyl substituent were prepared. The anthracene group acted as a reporting group for protonation at the nitrogen in the iminosugar because an unprotonated amine was found to quench fluorescence by photoinduced electron transfer. The new compounds were found to inhibit β-glucosidase from Phanerochaete chrysosporium and α-glucosidase from Aspergillus niger, with K_i values in the low micro- to nanomolar range. Fluorescence and inhibition versus pH studies of the β-glucosidase–iminosugar complexes revealed that the amino group in the inhibitor is unprotonated when bound, while one of the active site carboxylates is protonated.

中文翻译：

使用光诱导电子转移测定亚氨基糖-酶复合物的质子化状态

制备了一系列在N-烷基取代基中含有荧光10-氯-9-蒽基团的1-脱氧野尻霉素的N-烷基化类似物。蒽基团充当亚氨基糖中氮原子质子化的报告基团，因为发现未质子化的胺通过光诱导电子转移来猝灭荧光。研究发现，这些新化合物可抑制黄孢原毛平革菌 (Phanerochaete chrysosporium ) 的 β-葡萄糖苷酶和黑曲霉 (Aspergillus niger)的 α-葡萄糖苷酶， K _i值在微摩尔至纳摩尔范围内。 β-葡萄糖苷酶-亚氨基糖复合物的荧光和抑制与pH 值研究表明，抑制剂中的氨基在结合时是非质子化的，而活性位点之一的羧酸盐是质子化的。

更新日期：2017-09-14

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