Department of Chemistry and Biochemistry , Central Michigan University , Mount Pleasant , Michigan 48859 , United States.
Department of Chemistry , University of Southern Maine , Portland , Maine 04104 , United States.
J Org Chem. 2018 Aug 3;83(15):8662-8667. doi: 10.1021/acs.joc.8b00810. Epub 2018 Jul 23.
Trehalosamine (2-amino-2-deoxy-α,α-d-trehalose) is an aminoglycoside with antimicrobial activity against Mycobacterium tuberculosis, and it is also a versatile synthetic intermediate used to access imaging probes for mycobacteria. To overcome inefficient chemical synthesis approaches, we report a two-step chemoenzymatic synthesis of trehalosamine that features trehalose synthase (TreT)-catalyzed glycosylation as the key transformation. Soluble and recyclable immobilized forms of TreT were successfully employed. We demonstrate that chemoenzymatically synthesized trehalosamine can be elaborated to two complementary imaging probes, which label mycobacteria via distinct pathways.
海藻糖胺（2-氨基-2-脱氧-α,α-海藻糖）是一种具有抗结核分枝杆菌活性的氨基糖苷类药物，也是一种通用的合成中间体，可用于获取分枝杆菌的成像探针。为了克服化学合成方法效率低下的问题，我们报告了海藻糖胺的两步化学酶法合成，其中海藻糖合酶（TreT）催化的糖基化是关键转化。成功地使用了可溶性和可回收的固定化 TreT 形式。我们证明，化学酶法合成的海藻糖胺可以进一步衍生为两种互补的成像探针，它们通过不同的途径标记分枝杆菌。
