Cheng, B.Dong, L.Zhu, Y.Huang, R.Sun, Y.You, Q.Song, Q.Paton, J.C.Paton, A.W.Chen, X.2025-08-062025-08-062019ACS Chemical Biology, 2019; 14(10):2141-21471554-89291554-8937https://hdl.handle.net/2440/146542Neu5Ac, Neu5Gc, and KDN are three forms of sialic acids in vertebrates that possess distinct biological functions. Herein, we report the synthesis and metabolic incorporation of the 9-azido analogues of three sialic acid forms in mammalian cells. The incorporated sialic acid analogues enable fluorescent imaging of cell-surface sialoglycans and proteomic profiling of sialoglycoproteins. Furthermore, we apply them to metabolically engineer cell surfaces with sialoglycans terminated with distinct sialic acids or their 9-azido analogues. The remodeled cells expressing specific cell-surface sialoglycoforms show distinct binding affinity toward subtilase cytotoxin (SubAB), a toxin secreted by Shiga toxigenic Escherichia coli. The 9-azido analogues of sialic acid forms developed in this work provide a versatile tool for metabolic remodeling of cell-surface properties and modulating pathogen−host interactions.en© 2019 American Chemical SocietyAzides; Carbohydrates; Chemical biology; Fluorescence; LabelingCell Line, TumorCHO CellsVero CellsAnimalsHumansCricetulusAzidesSialic AcidsSubtilisinsSialoglycoproteinsEscherichia coli ProteinsMembrane GlycoproteinsProteomicsCell EngineeringChlorocebus aethiopsJournal article10.1021/acschembio.9b00556499268Paton, J.C. [0000-0001-9807-5278]