A Photocaged Azidosugar for Light-Controlled Metabolic Labeling of Cell-Surface Sialoglycans
A Photocaged Azidosugar for Light-Controlled Metabolic Labeling of Cell-Surface Sialoglycans
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DOI：
10.1002/cjoc.202100748
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发表时间：
2022-01-22
影响因子：
5.4
通讯作者：
Chen, Xing
中科院分区：
文献类型：
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作者：
Cheng, Bo;Wan, Yi;Chen, Xing
综合概述光笼化策略已被广泛用于激活生物分子，从而以高时间和空间分辨率调节潜在的生物过程。在这里，我们将这一策略整合到代谢多聚糖标记中，这使得能够用叠氮化合物对细胞表面唾液酸聚糖进行光学控制的代谢标记。N-叠氮乙酰甘露糖胺(ManNAz)被笼化在4，5-二甲氧基-2-硝基苄基(DMNB)的异构羟基上，以阻断其细胞代谢。饲喂细胞后，365 nm紫外光或405 nm可见光照射使光笼裂解，并在细胞内产生ManNAz。ManNAz在代谢过程中转化为叠氮唾液酸，然后将其结合到细胞表面的唾液酸中。我们通过在单个细胞上特异地标记唾液酸聚糖和基于光触发脉冲追逐标记来跟踪ManNAz的新陈代谢，展示了这一策略的空间和时间控制。光控制的代谢多糖标记策略应该有助于以高时空精度探测复杂生物系统中的糖基化。
Comprehensive Summary The photocaging strategy has been widely used for activating biomolecules and hence regulating the underlying biological processes with high temporal and spatial resolution. Herein, we integrate this strategy into metabolic glycan labeling, which enables optically-controlled metabolic labeling of cell-surface sialoglycans with azides. N-Azidoacetylmannosamine (ManNAz) is caged with a 4,5-dimethoxy-2-nitrobenzyl (DMNB) group at the anomeric hydroxyl group to block its cellular metabolism. After feeding to the cells, irradiation with 365 nm UV light or 405 nm visible light cleaves the photocage and generates ManNAz within the cells. ManNAz is metabolically converted to azido sialic acid, which is then incorporated into cell-surface sialoglycans. We demonstrated spatial and temporal control of this strategy by specifically labeling sialoglycans on a single cell and tracking the metabolism of ManNAz based on light-triggered pulse-chase labeling, respectively. The light-controlled metabolic glycan labeling strategy should facilitate probing of glycosylation in complex biological systems with high spatiotemporal precision.