9-Azido Analogues of Three Sialic Acid Forms for Metabolic Remodeling of Cell-Surface Sialoglycans.

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dc.contributor.authorCheng, B.
dc.contributor.authorDong, L.
dc.contributor.authorZhu, Y.
dc.contributor.authorHuang, R.
dc.contributor.authorSun, Y.
dc.contributor.authorYou, Q.
dc.contributor.authorSong, Q.
dc.contributor.authorPaton, J.C.
dc.contributor.authorPaton, A.W.
dc.contributor.authorChen, X.
dc.date.issued2019
dc.description.abstractNeu5Ac, 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.
dc.description.statementofresponsibilityBo Cheng, Lu Dong, Yuntao Zhu, Rongbing Huang, Yuting Sun, Qiancheng You, Qitao Song, James C. Paton, Adrienne W. Paton, and Xing Chen
dc.identifier.citationACS Chemical Biology, 2019; 14(10):2141-2147
dc.identifier.doi10.1021/acschembio.9b00556
dc.identifier.issn1554-8929
dc.identifier.issn1554-8937
dc.identifier.orcidPaton, J.C. [0000-0001-9807-5278]
dc.identifier.urihttps://hdl.handle.net/2440/146542
dc.language.isoen
dc.publisherAmerican Chemical Society
dc.rights© 2019 American Chemical Society
dc.source.urihttps://doi.org/10.1021/acschembio.9b00556
dc.subjectAzides; Carbohydrates; Chemical biology; Fluorescence; Labeling
dc.subject.meshCell Line, Tumor
dc.subject.meshCHO Cells
dc.subject.meshVero Cells
dc.subject.meshAnimals
dc.subject.meshHumans
dc.subject.meshCricetulus
dc.subject.meshAzides
dc.subject.meshSialic Acids
dc.subject.meshSubtilisins
dc.subject.meshSialoglycoproteins
dc.subject.meshEscherichia coli Proteins
dc.subject.meshMembrane Glycoproteins
dc.subject.meshProteomics
dc.subject.meshCell Engineering
dc.subject.meshChlorocebus aethiops
dc.title9-Azido Analogues of Three Sialic Acid Forms for Metabolic Remodeling of Cell-Surface Sialoglycans.
dc.typeJournal article
pubs.publication-statusPublished

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