Here we describe chemical methods for converting thioamide-containing peptides and proteins to corresponding oxoamide derivatives. In this way, isotopically labeled oxygen atoms can be incorporated site specifically. This chemistry can also be used to convert fluorescently tagged biomacromolecules bearing thiourea functional groups into oxygen-containing ureas. These modifications enable a variety of biophysical studies including some of those that employ advanced vibrational spectroscopy, fluorescence, or mass spectrometry techniques. Our approach allows for functionalization of thiocarbonyl bonds in such a way that oxygen-16, -17, or -18 isotopes can be incorporated from a common precursor with minimal purification. Applications to small model systems will be presented.

Desulfurization of thioamide containing peptides and proteins for biophysical studies

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