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The results indicate that the mechanism of the cyanuration reaction is a nucleophilic aromatic substitution of the S<jats:sc>N<\/jats:sc>2 type, where the tyrosine oxygen acts as a nucleophile and the displacement takes places at a carbon atom which is part of the six\u2010membered ring of the <jats:italic>s<\/jats:italic>\u2010triazene. This reaction must compete with the hydrolysis of cyanuric fluoride in aqueous media. These competing reactions generate curves for the pH dependence of the reactivity of tyrosine with cyanuric fluoride whihc vary in a predictable manner with the extent of ionization of tyrosine and the concentration of cyanuric fluoride. In the case of proteins, the dependence of the degree of tyrosine reactivity on pH and temperature within the pH range of full reactivity of the free amino acid reflects constraints imposed by the microenvironment of these groups within the three\u2010dimensional structure of the macromolecule.<\/jats:p>","DOI":"10.1002\/bip.1972.360111104","type":"journal-article","created":{"date-parts":[[2004,12,30]],"date-time":"2004-12-30T00:33:00Z","timestamp":1104366780000},"page":"2233-2240","source":"Crossref","is-referenced-by-count":4,"title":["The pH dependence of tyrosine cyanuration in proteins"],"prefix":"10.1002","volume":"11","author":[{"given":"Marina J.","family":"Gorbunoff","sequence":"first","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2004,2]]},"reference":[{"key":"e_1_2_1_2_2","doi-asserted-by":"publisher","DOI":"10.1016\/0006-3002(63)91419-7"},{"key":"e_1_2_1_3_2","doi-asserted-by":"publisher","DOI":"10.1146\/annurev.bi.36.070167.000305"},{"key":"e_1_2_1_4_2","first-page":"506","volume-title":"Methods in Enzymology","author":"Gorbunoff M. 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