用生物正交化学探测分枝杆菌海藻糖代谢物。

Department of Chemistry, University of California, Berkeley, California 94720, USA.

J Am Chem Soc. 2012 Oct 3;134(39):16123-6. doi: 10.1021/ja3062419. Epub 2012 Sep 24.

Mycobacteria, including the pathogen Mycobacterium tuberculosis, use the non-mammalian disaccharide trehalose as a precursor for essential cell-wall glycolipids and other metabolites. Here we describe a strategy for exploiting trehalose metabolic pathways to label glycolipids in mycobacteria with azide-modified trehalose (TreAz) analogues. Subsequent bioorthogonal ligation with alkyne-functionalized probes enabled detection and visualization of cell-surface glycolipids. Characterization of the metabolic fates of four TreAz analogues revealed unique labeling routes that can be harnessed for pathway-targeted investigation of the mycobacterial trehalome.

分枝杆菌，包括病原体结核分枝杆菌，将非哺乳动物二糖海藻糖用作必需细胞壁糖脂和其他代谢物的前体。在这里，我们描述了一种利用海藻糖代谢途径的策略，用叠氮修饰的海藻糖 (TreAz) 类似物标记分枝杆菌中的糖脂。随后与炔基功能化探针进行生物正交连接，可实现细胞表面糖脂的检测和可视化。对四种 TreAz 类似物的代谢命运的表征揭示了独特的标记途径，可以用于靶向分枝杆菌海藻糖组的途径研究。