A hydrophilic azacyclooctyne for Cu-free click chemistry

被引：213

作者：

Sletten, Ellen M.

Bertozzi, Carolyn R. ^{[1
]}

机构：

[1] Univ Calif Berkeley, Lawrence Berkeley Lab, Dept Chem, Berkeley, CA 94720 USA

来源：

ORGANIC LETTERS | 2008年 / 10卷 / 14期

关键词：

D O I：

10.1021/ol801141k

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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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页码：3097 / 3099

页数：3

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