Zeitschrift für Chromatographie und Trenntechniken
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Notes on Synthesis of Perdeutero-5-¹³C,5,5,5-Trifluoroisoleucine VI⁵⁶

Naugler DG and Prosser RS

The ¹³CF₃ group is a promising label for heteronuclear (¹⁹F,¹³C) NMR studies of proteins. Desirable locations for this NMR spin label include the branched chain amino acid methyl groups. It is known that replacement of CH₃ by CF₃ at such locations preserves protein structure and function and enhances stability. ¹³CF₃ may be introduced at the δ position of isoleucine and incorporated biosynthetically in highly deuterated proteins. This paper reports our work in synthesis and purification of 5,5,5-trifluoroisoleucine, its perdeutero and 5-¹³C versions and of 2-¹³C-trifluoroacetate and its utility as a precursor for introduction of the ¹³CF₃ group into proteins.