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A hydrophilic azacyclooctyne for Cu-free click chemistry.

Sletten EM, Bertozzi CR - Org. Lett. (2008)

Bottom Line: 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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Affiliation: Department 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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Synthesis of DIMAC
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A hydrophilic azacyclooctyne for Cu-free click chemistry.

Sletten EM, Bertozzi CR - Org. Lett. (2008)

Synthesis of DIMAC
© Copyright Policy - open-access - ccc-price
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC2664610&req=5

sch1: Synthesis of DIMAC
Bottom Line: 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.

View Article: PubMed Central - PubMed

Affiliation: Department 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.

Show MeSH