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- W3198068327 abstract "Diels-Alder chemistry is a well-explored avenue for the synthesis of bioactive materials; however, its potential applications have recently expanded following the development of reactions that can be performed in buffered aqueous environments at low temperatures, including fulvene-maleimide [4 + 2] cycloadditions. In this study, we synthesized two novel amine-reactive fulvene linkers to demonstrate the application of this chemistry for generating mass spectrometry-cleavable labels (mass tags), which can be used for the labeling and detection of proteins. Successful conjugation of these linkers to maleimide-labeled peptides was observed at low temperatures in phosphate-buffered saline, allowing the non-destructive modification of proteins with such mass tags. The labile nature of fulvene-maleimide adducts in the gas phase also makes them suitable for both matrix-assisted laser desorption/ionization (MALDI) and electrospray ionization (ESI) mass spectrometric analysis. Unlike previous examples of MALDI mass tags, we show that fulvene-maleimide cycloaddition adducts fragment predictably upon gas-phase activation without the need for bulky photocleavable groups. Further exploration of this chemistry could therefore lead to new approaches for mass spectrometry-based bioassays." @default.
- W3198068327 created "2021-09-13" @default.
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- W3198068327 date "2021-08-31" @default.
- W3198068327 modified "2023-09-27" @default.
- W3198068327 title "Retro Diels–Alder Fragmentation of Fulvene–Maleimide Bioconjugates for Mass Spectrometric Detection of Biomolecules" @default.
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- W3198068327 doi "https://doi.org/10.1021/acs.analchem.1c00193" @default.
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