Visualizing metabolically labeled glycoconjugates of living cells by copper-free and fast huisgen cycloadditions
Visualizing metabolically labeled glycoconjugates of living cells by copper-free and fast huisgen cycloadditions
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DOI：
10.1002/anie.200705456
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发表时间：
2008-01-01
影响因子：
16.6
通讯作者：
Boons, Geert-Jan
中科院分区：
文献类型：
--
作者：
Ning, Xinghai;Guo, Jun;Boons, Geert-Jan
叠氮化合物在生物体系中极为罕见，正逐渐成为一种极具吸引力的生物偶联化学柄。特别是CuI催化叠氮化合物与末端炔的1，3-偶极环化反应得到稳定的三唑[6，7]，已被用于标记各种生物分子，[8-12]基于活性的蛋白质图谱，[13]和微阵列和小分子文库的化学合成。[14]将叠氮化合物安装到生物分子中的一种有吸引力的方法是基于代谢标记，即利用细胞的生物合成机制将含有叠氮的生物合成前体结合到生物分子中。[15]这种方法已被用于用各种反应性探针标记生命系统的蛋白质、多糖和脂类。这些探针可以帮助绘制糖选择性糖蛋白的图谱，并识别糖基化位点。[16]乙炔探针也已用于叠氮修饰生物分子的细胞表面成像，一种特别吸引人的方法涉及通过[3+2]环加成反应从非荧光前体生成荧光探针。
Azides, which are extremely rare in biological systems, are emerging as attractive chemical handles for bioconjugation.[1–5] In particular, the CuI catalyzed 1, 3-dipolar cyclization of azides with terminal alkynes to give stable triazoles [6, 7] has been employed for the tagging of a variety of biomolecules,[8–12] activity-based protein profiling,[13] and the chemical synthesis of microarrays and small molecule libraries.[14]An attractive approach for installing azides into biomolecules is based on metabolic labeling whereby an azide-containing biosynthetic precursor is incorporated into biomolecules using the cells’ biosynthetic machinery.[15] This approach has been employed for tagging proteins, glycans, and lipids of living systems with a variety of reactive probes. These probes can facilitate the mapping of saccharide-selective glycoproteins and identify glycosylation sites.[16] Alkyne probes have also been used for cell surface imaging of azide-modified bio-molecules and a particularly attractive approach involves the generation of a fluorescent probe from a non-fluorescent precursor by a [3+ 2] cycloaddition.[17]