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Updated: Jul 4, 2026

Chemoselective Modification of Viral Surfaces via Bioorthogonal Click Chemistry
Published on: August 19, 2012
A hydrophilic azacyclooctyne for Cu-free click chemistry
Ellen M Sletten1, Carolyn R Bertozzi
1Department of Chemistry and Molecular and Cell Biology and Howard Hughes Medical Institute, University of California, California, USA.
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.
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