Premium
Simple preparation of new [ 18 F]F‐labeled synthetic amino acid derivatives with two click reactions in one‐pot and SPE purification
Author(s) -
Yook CheolMin,
Lee Sang Ju,
Oh Seung Jun,
Ha HyunJoon,
Lee Jong Jin
Publication year - 2015
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.3297
Subject(s) - chemistry , propyne , cycloaddition , click chemistry , yield (engineering) , alkyne , alkyl , solvent , chemical synthesis , organic chemistry , catalysis , biochemistry , materials science , metallurgy , in vitro
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.