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：

---

利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oji霉素的N-烷基化类似物。蒽基充当亚氨基糖中氮质子化的报告基团，因为发现未质子化的胺通过光诱导的电子转移来猝灭荧光。发现这些新化合物可抑制Phanerochaete chrysosporium的β-葡萄糖苷酶和黑曲霉的α-葡萄糖苷酶，其K _i值在低微摩尔至纳摩尔范围内。荧光和抑制与 对β-葡萄糖苷酶-亚氨基糖复合物的pH研究表明，结合时抑制剂中的氨基未质子化，而活性位点羧酸盐之一被质子化。