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ChemComm
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DOI: 10.1039/C8CC01715H
COMMUNICATION
Journal Name
12 S. Lee, H. Koo, J. H. Na, S. J. Han, H. S. Min, S. J. Lee, S. H.
Kim, S. H. Yun, S. Y. Jeong, I. C. Kwon, K. Choi and K. Kim, ACS
Nano, 2014, , 2048‐2063.
13 H. Wang, M. Gauthier, J. R. Kelly, R. J. Miller, M. Xu, W. D.
Conclusions
In this work, we demonstrate that the N‐methyl carbamate linker
incorporated on the anomeric position of ManNAz successfully
controlled the metabolic property of an unnatural sugar. The NN
linker completely blocked its metabolic processes when caged and
fully resumed its metabolic activity after being decaged. We
synthesized HQ‐NN‐AAM which was reduced by DTD/NADPH and
underwent a subsequent self‐immolative process to yield the active
metabolic species. The incorporation of unnatural sugars in cell
surface glycans was confirmed using HQ‐NN‐AAM as a labeling
reagent. The in vitro labeling experiments demonstrated the
specificity of HQ‐NN‐AAM that responded to DTD. This work not only
demonstrated DTD responsive metabolic labeling of the caged
precursor, but also provides deep insight into developing future
metabolically active species that respond to endogenous cues in
cells.
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Conflicts of interest
There are no conflicts to declare.
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Acknowledgement
J.C. acknowledges support from the United States National
Institute of Health Grant NIH‐R21 1R21CA198684 and
1R01CA207584. Research reported in this publication was
supported by the National Institute of Biomedical Imaging And
Bioengineering of the National Institutes of Health under Award
Number T32EB019944. The content is solely the responsibility
of the authors and does not necessarily represent the official
views of the National Institutes of Health.
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