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• W2028302845 endingPage "361" @default.
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• W2028302845 abstract "Site-selective labeling of endogenous proteins represents a major challenge in chemical biology, mainly due to the absence of unique reactive groups that can be addressed selectively. Recently, we have shown that surface-exposed lysine residues of two endogenous proteins and a peptide exhibit subtle changes in their individual reactivities. This feature allows the modification of a single residue in a highly site-selective fashion if kinetically controlled labeling conditions are applied. In order to broaden the scope of the “kinetically-controlled protein labeling” (KPL) approach and highlight additional applications, the water-soluble bioorthogonal reagent, biotin–TEO–azido–NHS (11), is developed which enables the site-selective introduction of an azido group onto endogenous proteins/peptides. This bioconjugation reagent features a biotin tag for affinity purification, an azido group for bioorthogonal labeling, a TEO (tetraethylene oxide) linker acting as a spacer and to impart water solubility and an N-hydroxysuccinimidyl (NHS) ester group for reacting with the exposed lysine residue. As a proof of concept, the native protein ribonuclease A (RNase A) bearing ten available lysine residues at the surface is furnished with a single azido group at Lys 1 in a highly site-selective fashion yielding azido–(K1)RNase A. The K1 site-selectivity is demonstrated by the combined application and interpretation of high resolution MALDI-ToF mass spectroscopy, tandem mass spectroscopy and extracted ion chromatography (XIC). Finally, the water soluble azide-reactive phosphine probe, rho–TEO–phosphine (21) (rho: rhodamine), has been designed and applied to attach a chromophore to azido–(K1)RNase A via Staudinger ligation at physiological pH indicating that the introduced azido group is accessible and could be addressed by other established azide-reactive bioorthogonal reaction schemes." @default.
• W2028302845 created "2016-06-24" @default.
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• W2028302845 date "2013-01-01" @default.
• W2028302845 modified "2023-10-15" @default.
• W2028302845 title "Site-selective azide incorporation into endogenous RNase A via a “chemistry” approach" @default.
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• W2028302845 doi "https://doi.org/10.1039/c2ob26561c" @default.
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