期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 137, 期 7, 页码 2412-2415出版社
AMER CHEMICAL SOC
DOI: 10.1021/ja5095815
关键词
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资金
- PhRMA Foundation
- NIH [T32 GM008688, R01 GM044783, P41 GM103399]
We introduce a stabilized diazo group as a reporter for chemical biology. ManDiaz, which is a diazo derivative of N-acetylmannosamine, is found to endure cellular metabolism and label the surface of a mammalian cell. There its diazo group can undergo a 1,3-dipolar cycloaddition with a strained alkyne, providing a signal comparable to that from the azido congener, ManNAz. The chemoselectivity of diazo and alkynyl groups enables dual labeling of cells that is not possible with azido and alkynyl groups. Thus, the diazo group, which is approximately half the size of an azido group, provides unique opportunities for orthogonal labeling of cellular components.
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