Isotopic labeling of tyrosine, followed by 17O n.m.r

A simple chemical procedure has been developed in order to introduce oxygen-17 labels into the carboxylic and phenolic sites of L-tyrosine. Detailed studies of the 17O n.m.r. chemical shift as a function of pH reveal an unusually large titration shift upon the deprotonation of the phenol group. This result suggests that 17O n.m.r. may contribute useful information about side chain properties in peptides and proteins.