A Hydrophilic Azacyclooctyne for Cu-Free Click Chemistry
Open Access
- 13 June 2008
- journal article
- research article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 10 (14), 3097-3099
- https://doi.org/10.1021/ol801141k
Abstract
Biomolecules labeled with azides can be detected through Cu-free click chemistry with cyclooctyne probes, but their intrinsic hydrophobicity can compromise bioavailability. Here, we report the synthesis and evaluation of a novel azacyclooctyne, 6,7-dimethoxyazacyclooct-4-yne (DIMAC). Generated in nine steps from a glucose analogue, DIMAC reacted with azide-labeled proteins and cells similarly to cyclooctynes. However, its superior polarity and water solubility reduced nonspecific binding, thereby improving the sensitivity of azide detection.Keywords
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