1309935-53-2Relevant academic research and scientific papers
SiFA-modified phenylalanine: A key compound for the efficient synthesis of 18F-labelled peptides
Iovkova, Ljuba,Koenning, Daniel,Waengler, Bjoern,Schirrmacher, Ralf,Schoof, Sebastian,Arndt, Hans-Dieter,Jurkschat, Klaus
, p. 2238 - 2246 (2011/08/03)
Both the racemic and the stereoselective synthesis of the silicon-modified amino acid p-(tBu2FSi)C6H4CH 2(NH2)COOH (SiFA-phenylalanine, 6) and its derivatives p-(tBu2FSi)C6H4CH2(NHBoc)COOH (10) and p-(tBu2FSi)C6H4CH2(NHFmoc)COOH (11) are reported. The latter two compounds are valuable building blocks for the convenient introduction of silicon-based fluoride acceptors (SiFAs) into peptides by solid-phase peptide syntheses (SPPS). As prove of principle, the Tyr3-octreotate derivatives 12, 13 and 14 were prepared by using standard protocols of the solid-phase peptide synthesis (SPPS). They were labelled with 18F-fluorine by isotopic exchange in radiochemical yields of up to 70 % (with radiochemical purity ranging between 92 and 99 %). The incorporation of 18F-fluorine into the SiFA-modified amino acid 6 was studied as the latter may also serve as a tracer in PET. After purification, [18F]-6 showed a remarkable stability in an isotonic solution. Also reported is the molecular structure, as determined by single-crystal X-ray diffraction analysis, of p-(tBu2FSi)C 6H4CHCH[C(O)OMe]NHC(O)OCH2Ph (8), which serves as a precursor for the stereoselective synthesis of compound 6.
