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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

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A hydrophilic azacyclooctyne for Cu-free click chemistry.

Sletten Ellen M EM Bertozzi Carolyn R CR

Organic letters 20080613 14

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, thereb ...[more]

PMID: 18549231

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