The Bücherer-Strecker synthesis of D- and L-(1-11C)tyrosine and the in vivo study of L-(1-11C)tyrosine in human brain using positron emission tomography.
The synthesis of D- and L-(1-11C)tyrosine, starting with 11C-cyanide, is reported. DL-(1-11C)Tyrosine was prepared by the Bücherer-Strecker reaction, from carrier added 11C-cyanide with an incorporation of 80% in 20 min. The isolation of the pure D- and L-amino acid isomers from the enantiomeric mixture was accomplished within 15 min by preparative HPLC using a chiral stationary phase and a phosphate buffer as the mobile phase. Typically, the total synthesis time was 50 min (including purification) from end of trapping of 11C-cyanide, with a radiochemical yield of D- and L-amino acid of 40%-60%. The D- and L-(1-11C)tyrosine were both obtained optically pure, with a carrier added specific activity of 0.3-0.5 Ci/mmol and a radiochemical purity better than 99%. The 11C labelled L-tyrosine was used in an in vivo study in the human brain using positron emission tomography (PET).
D001921:Brain / Q000000981:diagnostic imaging*; D002250:Carbon Radioisotopes; D006801:Humans; D013237:Stereoisomerism; D014055:Tomography, Emission-Computed; D014443:Tyrosine / Q000138:chemical synthesis
D002250:Carbon Radioisotopes; D014443:Tyrosine