A Photocaged Azidosugar for Light-Controlled Metabolic Labeling of Cell-Surface Sialoglycans  

作　　者：Bo Cheng Yi Wan Qi Tang Yifei Du Feiyang Xu Zhimin Huang Wei Qin Xing Chen 

机构地区：[1]College of Chemistry and Molecular Engineering,Peking University,Beijing 100871,China [2]Beijing National Laboratory for Molecular Sciences,Peking University,Beijing 100871,China [3]Peking-Tsinghua Center for Life Sciences,Peking University,Beijing 100871,China [4]Synthetic and Functional Biomolecules Center Peking University,Beijing 100871,China [5]Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education,Peking University,Beijing 100871,China

出　　处：《Chinese Journal of Chemistry》2022年第7期806-812,共7页中国化学（英文版）

基　　金：supported by the National Key R&D Program of China(No.2018YFA0507600);the National Natural Science Foundation of China(Nos.91753206 and 21521003)。

摘　　要：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 optical-ly-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.

关 键 词：Sialic acids Caged compounds Click chemistry PULSE-CHASE Single cell 

分 类 号：O62[理学—有机化学]