Abstract
In this study, we report incorporation of a covalent linker at the anomeric position of N-azidoacetylmannosamine (ManNAz) for caging its metabolic process. We synthesized a DT-diaphorase-responsive metabolic precursor, HQ-NN-AAM, using an optimized linker. The caged metabolite showed responsiveness to DT-diaphorase in vitro, resulting in metabolic incorporation of an azido sugar into the cell surface in multiple cell lines.
MeSH terms
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Azides / chemical synthesis
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Azides / chemistry
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Azides / metabolism*
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Cell Line, Tumor
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Cell Tracking / methods*
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Click Chemistry
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Ethylenediamines / chemistry
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Glycosylation
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Hexosamines / chemical synthesis
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Hexosamines / chemistry
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Hexosamines / metabolism*
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Humans
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NAD(P)H Dehydrogenase (Quinone) / metabolism*
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Polysaccharides / biosynthesis*
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Quinones / chemical synthesis
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Quinones / chemistry
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Quinones / metabolism*
Substances
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Azides
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Ethylenediamines
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Hexosamines
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N-azidoacetylmannosamine
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Polysaccharides
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Quinones
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dimethylethylenediamine
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NAD(P)H Dehydrogenase (Quinone)