Site-Specific Labeling of Proteins and Peptides withTrans-cyclooctene Containing Handles Capable of Tetrazine Ligation
نویسندگان
چکیده
منابع مشابه
Fast and sensitive pretargeted labeling of cancer cells through a tetrazine/trans-cyclooctene cycloaddition.
There is considerable interest in the use of bioorthogonal covalent chemistry, such as “click” reactions, to label small molecules located on live or fixed cells. Such labeling has been used for the visualization of glycans, activity-based protein profiling, the site-specific tagging of proteins, the detection of DNA and RNA synthesis, investigation of the fate of small molecules in plants, and...
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Computation has guided the design of conformationally-strained dioxolane-fused trans-cyclooctene (d-TCO) derivatives that display excellent reactivity in the tetrazine ligation. A water soluble derivative of 3,6-dipyridyl-s-tetrazine reacts with d-TCO with a second order rate k2 366,000 (+/- 15,000) M-1s-1 at 25 °C in pure water. Furthermore, d-TCO derivatives can be prepared easily, are access...
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The development of fluorogenic reactions which lead to the formation of fluorescent products from two nonfluorescent starting materials is highly desirable, but challenging. Reported herein is a new concept of fluorescent product formation upon the inverse electron-demand Diels-Alder reaction of 1,2,4,5-tetrazines with particular trans-cyclooctene (TCO) isomers. In sharp contrast to known fluor...
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In the last few years, the use of labeled proteins has significantly expanded in the life sciences. Now, labeled proteins are indispensable tools for a wide spectrum of biophysical and chemical biology applications. In particular, the quest for more sophisticated experimental setups requires the development of new synthetic methodology, especially for multiple site-specific labeling. In this pa...
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Rapid, one-pot, concerted, site-specific labeling of proteins at genetically encoded unnatural amino acids with distinct small molecules at physiological pH, temperature, and pressure is an important challenge. Current approaches require sequential labeling, low pH, and typically days to reach completion, limiting their utility. We report the efficient, genetically encoded incorporation of alky...
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ژورنال
عنوان ژورنال: Chemical Biology & Drug Design
سال: 2014
ISSN: 1747-0277
DOI: 10.1111/cbdd.12303