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Fluorescence quenching by the formation of an intramolecular fluorophore–tyrosine complex is relieved upon phosphorylation. Substrates 11 (where Dap = L-2,3-diaminopropionic acid) and 12 (where Dab = L-2,4-diaminobutanoic acid) display a 4.3- and 4.7-fold enhancement in fluorescence, respectively, upon phosphorylation. Pronounced NOEs between the pyrene and tyrosine protons are displayed in 11 but not in the phosphorylated analogue 13.
