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Irradiation of diazirines with UV light (ca. 350-360 nm) yields a highly reactive carbene species that can undergo insertions into C–C, C–H, O–H, and X–H (X = heteroatom) bonds of neighboring molecules to irreversibly form a covalent bond.
The diazirine moiety is the smallest of all photophores, so introduction of a diazirine-bearing amino acid into a peptide or protein usually does not impair its biological activity. Further advantages of diazirine crosslinkers are their stability at room temperature and their relative stability against nucleophiles as well as towards both acidic and basic conditions.
