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. 2024 Jun 10;15:4648. doi: 10.1038/s41467-024-48604-7

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© The Author(s) 2024

Open Access This article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons licence, and indicate if changes were made. The images or other third party material in this article are included in the article’s Creative Commons licence, unless indicated otherwise in a credit line to the material. If material is not included in the article’s Creative Commons licence and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this licence, visit http://creativecommons.org/licenses/by/4.0/.

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Fig. 1 — a Chemical structure of the synthesized TAMRA-based probes. b Aldehyde-ligation reaction types and corresponding reaction rate constants relative to the commercially available TMR-HZD. The rate constant of the oxyamine probe (TMR-O) is 27-fold higher than TMR-HZD. c–h Reaction rates of the probes with butyraldehyde were followed by HPLC with fluorescence detection. HPLC traces for the forward (c, e, g) and reverse (d, f, h) reactions for TMR-HZD, TMR-HZN and TMR-O with butyraldehyde showing the ligation product (orange) and the free, unbound probe (blue). Of note, the HPLC traces for the commercially available TMR-HZD (c, d) also contain a small unidentified impurity (black). i Plots of the observed rate constant for the formation of the aldehyde-ligation products, (j) the corresponding percent conversion as a function of time and, (k) the percent product generated at 100 min. The non-binding control probe (TMR-NB), in which a cyclic piperazine group replaces the reactive hydrazine, shows no reactivity, confirming the specificity of the oxyamine (TMR-O), hydrazine (TMR-HZN) and pyrrole (TMR-Pyr) based TAMRA probes for aldehydes. TMR-O, however, has the fastest reactivity and highest percent conversion to ligation product. Values are plotted as the average of three experiments ± standard deviation. Source data are provided in the Source Data file.