A fluorogenic probe for the catalyst-free detection of azide-tagged molecules.
A fluorogenic probe for the catalyst-free detection of azide-tagged molecules.
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DOI：
10.1021/ja309000s
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发表时间：
2012-11-14
影响因子：
15
通讯作者：
Boons, Geert-Jan
中科院分区：
文献类型：
--
作者：
Friscourt, Frederic;Fahrni, Christoph J.;Boons, Geert-Jan
非荧光或弱荧光试剂产生高荧光产物的荧光反应可用于检测包括生物分子和材料在内的广泛化合物。我们描述了一种改性的二苯并环辛炔，在无催化剂的条件下进行快速应变促进与叠氮化物的环加成，产生强荧光三唑。与起始环辛炔相比，环加成产物的亮度超过1000倍，表现出大的斯托克斯位移，并且可以在350 nm以上激发，这是许多应用所需的。量子力学计算表明，三唑形成后的荧光增加是由于<->在平面C2 v-对称起始材料中的S 0-S1跃迁的振子强度相比于非平面环加成产物的破环和非平面环加成产物有很大的差异。这种新的荧光探针被成功地用于标记由叠氮基团修饰的蛋白质。
Fluorogenic reactions in which non- or weakly-fluorescent reagents produce highly fluorescent products can be exploited to detect a broad range of compounds including biomolecules and materials. We describe a modified dibenzocyclooctyne that under catalyst-free conditions undergoes fast strain-promoted cycloadditions with azides to yield strongly fluorescent triazoles. The cycloaddition products are more than 1000-fold brighter compared to the starting cyclooctyne, exhibit large Stokes shift, and can be excited above 350 nm, which is required for many applications. Quantum mechanical calculations indicate that the fluorescence increase upon triazole formation is due to large differences in oscillator strengths of the S0 <–> S1 transitions in the planar C2v-symmetric starting material compared to the symmetry-broken and non-planar cycloaddition products. The new fluorogenic probe was successfully employed for labeling of proteins modified by an azide moiety.
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影响因子：
46.2
作者：
Jewett JC;Bertozzi CR
通讯作者：
Bertozzi CR
影响因子：
16.6
作者：
Ning, Xinghai;Guo, Jun;Boons, Geert-Jan
通讯作者：
Boons, Geert-Jan
影响因子：
4.4
作者：
Improta, Roberto;Scalmani, Giovanni;Barone, Vincenzo
通讯作者：
Barone, Vincenzo
影响因子：
4.4
作者：
Improta, Roberto;Barone, Vincenzo;Frisch, Michael J.
通讯作者：
Frisch, Michael J.
影响因子：
15
作者：
Kennedy, David C.;McKay, Craig S.;Pezacki, John Paul
通讯作者：
Pezacki, John Paul