Kuhn C S, Lehmann J, Sandhoff K
Institut für Organische Chemie und Biochemie, Universität Freiburg, Germany.
Bioconjug Chem. 1992 May-Jun;3(3):230-3. doi: 10.1021/bc00015a005.
Two photolabile thioglycosides (8 and 9) were synthesized by Koenigs-Knorr type glycosylation. These compounds, being enzyme-resistant analogues of N-acetylhexosaminides, were shown to be good competitive inhibitors of lysosomal beta-hexosaminidase (2-acetamido-2-deoxy- beta-D-hexoside acetamidodeoxyhexohydrolase, EC 3.2.1.52) action. For photoaffinity labeling 3H-labeled 8a was prepared by enzymatic oxidation with galactose oxidase followed by reduction with sodium [3H]borohydride. Compound 8a, when photolyzed in the presence of hexosaminidase, specifically labeled both subunits of the enzyme.
通过柯尼希斯-克诺尔型糖基化反应合成了两种光不稳定硫代糖苷（8和9）。这些化合物作为N-乙酰己糖胺的酶抗性类似物，被证明是溶酶体β-己糖胺酶（2-乙酰氨基-2-脱氧-β-D-己糖苷乙酰氨基脱氧己糖水解酶，EC 3.2.1.52）作用的良好竞争性抑制剂。为了进行光亲和标记，通过半乳糖氧化酶的酶促氧化，然后用[3H]硼氢化钠还原，制备了3H标记的8a。当化合物8a在己糖胺酶存在下进行光解时，它特异性地标记了该酶的两个亚基。
