A hydrophilic azacyclooctyne for Cu-free click chemistry.

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.

SUBMITTER: Sletten EM 

PROVIDER: S-EPMC2664610 | biostudies-literature | 2008 Jul

REPOSITORIES: biostudies-literature