Nitration of Tyrosines

Tetranitromethane (TNM) reacts with the phenolic side chain of tyrosine under relatively mild conditions to give 3-nitrotyrosine ( 1 ). The protocol described in this chapter was developed for an anti-DNP antibody, but can be used with any other antibody or protein. The major side reaction is oxidation of thiols although under more extreme conditions tryptophans and methionines might be oxidized as well. As the reactive species is the phenolate ion, the main factor controlling the reactivity of protein tyrosyl side chains toward nitration by TNM is pH. Increasing the pH will usually enhance the rate of modification. These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.