Microwave enhanced synthesis of halogenated derivatives of L-tyrosine labeled with deuterium in aromatic ring

Abstract

AbstractThree halogenated derivatives of L-tyrosine, selectively labeled with deuterium in aromatic ring, i.e., 3′-fluoro-[5′-2H]-, 3′-chloro-[5′-2H]-, and 3′-iodo-[2′,5′-2H2]-L-tyrosine, were synthesized using microwave assisted acid-catalyzed isotope exchange between 3′-fluoro-, 3′-chloro- and 3′-iodo-L-tyrosine and heavy water. The degree of deuterium incorporation was confirmed by 1H NMR spectroscopy. The spectroscopic data indicate that isotope exchange depends on the method of heating and the power of microwaves. The deuterium enrichment of 3′-fluoro-[5′-2H]- and 3′-chloro-[5′-2H]-L-tyrosine amounted to 70% and 60%, respectively, while for 3′-iodo-[2′,5′-2H2]-L-tyrosine this value was about 50% and 95% for the 2′- and 5′-position. The isotopomers were obtained in good chemical yields of 50–70%.