一种用于活细胞中预靶向 Diels-Alder 生物正交标记的最小、无张力 S-烯丙基手柄。
A Minimal, Unstrained S-Allyl Handle for Pre-Targeting Diels-Alder Bioorthogonal Labeling in Live Cells.
机构信息
Department of Chemistry, University of Cambridge, Lensfield Road, CB2 1EW, Cambridge, UK.
Instituto de Medicina Molecular, Faculdade de Medicina, Universidade de Lisboa, Avenida Professor Egas Moniz, 1649-028, Lisboa, Portugal.
出版信息
Angew Chem Int Ed Engl. 2016 Nov 14;55(47):14683-14687. doi: 10.1002/anie.201608438. Epub 2016 Oct 20.
The unstrained S-allyl cysteine amino acid was site-specifically installed on apoptosis protein biomarkers and was further used as a chemical handle and ligation partner for 1,2,4,5-tetrazines by means of an inverse-electron-demand Diels-Alder reaction. We demonstrate the utility of this minimal handle for the efficient labeling of apoptotic cells using a fluorogenic tetrazine dye in a pre-targeting approach. The small size, easy chemical installation, and selective reactivity of the S-allyl handle towards tetrazines should be readily extendable to other proteins and biomolecules, which could facilitate their labeling within live cells.
未受应变的 S-烯丙基半胱氨酸氨基酸被特异性地安装在细胞凋亡蛋白生物标志物上，并进一步被用作 1,2,4,5-四嗪的化学接头和连接伙伴，通过逆电子需求 Diels-Alder 反应。我们通过使用前靶向方法中的荧光素四嗪染料，展示了这个最小接头在有效标记凋亡细胞方面的实用性。S-烯丙基接头的小尺寸、易于化学安装以及对四嗪的选择性反应性，应该很容易扩展到其他蛋白质和生物分子，这可以促进它们在活细胞内的标记。
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