9-Azido Analogues of Three Sialic Acid Forms for Metabolic Remodeling of Cell-Surface Sialoglycans.
Date
2019
Authors
Cheng, B.
Dong, L.
Zhu, Y.
Huang, R.
Sun, Y.
You, Q.
Song, Q.
Paton, J.C.
Paton, A.W.
Chen, X.
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Journal article
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ACS Chemical Biology, 2019; 14(10):2141-2147
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Bo Cheng, Lu Dong, Yuntao Zhu, Rongbing Huang, Yuting Sun, Qiancheng You, Qitao Song, James C. Paton, Adrienne W. Paton, and Xing Chen
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Abstract
Neu5Ac, 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.
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© 2019 American Chemical Society