title: Simple preparation of new [(18) F]F-labeled synthetic amino acid derivatives with two click reactions in one-pot and SPE purification.
abstract: New [(18) F]fluorinated 1,2,3-triazolyl amino acid derivatives were efficiently prepared from Huisgen 1,3-dipolar cycloaddition reactions, well known as click reaction. We developed two simultaneous click reactions in one-pot with a simple solid-phase extraction (SPE) purification method. [(18) F]fluoro-1-propyne was obtained at a 45% non-decay corrected radiochemical yield based on the [(18) F]fluoride ion. The one-pot and simultaneous two click reactions were performed with unprotected azido-alkyl amino acid, [(18) F]fluoro-1-propyne, and lipophilic additive alkyne to produce three synthetic amino acid derivatives, AMC-101 ([(18) F]-6a), AMC-102 ([(18) F]-6b), and AMC-103 ([(18) F]-6c) with 29%, 28%, and 24% of non-decay corrected radiochemical yields, respectively. All radiotracers indicated that radiochemical purities were >95% without any residual organic solvent. Our new method involving two click reactions in one-pot showed high radiochemical and chemical purity by easy removal of the residual precursor from the simultaneous two click reactions.
authors.affiliation: Department of Chemistry, Hankuk University of Foreign Studies, Yongin, Kyunggi-do, 449-719, South Korea.
authors.forename: Cheol-Min
authors.initials: CM
authors.lastname: Yook
authors.affiliation: Department of Nuclear Medicine, Asan Medical Center, University of Ulsan College of Medicine, 388-1 Pungnap-dong, Songpa-gu, Seoul, 138-736, South Korea.
authors.forename: Sang Ju
authors.initials: SJ
authors.lastname: Lee
authors.affiliation: Department of Nuclear Medicine, Asan Medical Center, University of Ulsan College of Medicine, 388-1 Pungnap-dong, Songpa-gu, Seoul, 138-736, South Korea.
authors.forename: Seung Jun
authors.initials: SJ
authors.lastname: Oh
authors.affiliation: Department of Chemistry, Hankuk University of Foreign Studies, Yongin, Kyunggi-do, 449-719, South Korea.
authors.forename: Hyun-Joon
authors.initials: HJ
authors.lastname: Ha
authors.affiliation: Department of Nuclear Medicine, Asan Medical Center, University of Ulsan College of Medicine, 388-1 Pungnap-dong, Songpa-gu, Seoul, 138-736, South Korea.
authors.forename: Jong Jin
authors.initials: JJ
authors.lastname: Lee
mesh_terms: D000596:Amino Acids / Q000737:chemistry*; D005462:Fluorine Radioisotopes / Q000737:chemistry*; D006845:Hydrocarbons, Fluorinated / Q000138:chemical synthesis*; D007553:Isotope Labeling / Q000379:methods*; D049268:Positron-Emission Tomography / Q000379:methods; D011854:Radiochemistry; D019275:Radiopharmaceuticals / Q000737:chemistry*; D052616:Solid Phase Extraction / Q000379:methods*
chemical_list: D000596:Amino Acids; D005462:Fluorine Radioisotopes; D006845:Hydrocarbons, Fluorinated; D019275:Radiopharmaceuticals
keywords: [18F]fluorination; amino acid; click reaction; positron emission tomography; solid-phase extraction