Journal
APPLIED RADIATION AND ISOTOPES
Volume 152, Issue -, Pages 172-179Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.apradiso.2019.06.039
Keywords
Radiolabeling; Fluoromethyl tosylate; Protected tryptophan; Alkylation; Challenges
Categories
Funding
- Australian Research Council Australia [LP130100703]
- Australian Research Council [LP130100703] Funding Source: Australian Research Council
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The reaction of [F-18]fluoromethyl tosylate with methyl(tert-butoxycarbonyl)-L-tryptophanate results in formation the 0-alltylated ester of the tryptophan instead of alkylation of the indole nitrogen of tryptophan as initially anticipated. Treatment of protected tryptophan with NaH in dimethyl formamide (DMF) along with [F-18] fluoromethyl tosylate at 130 degrees C results in the formation of [F-18]fluoromethyl(tert-butoxycarbonyl)-L-tryptophanate. Preferential formation of the O-alkylated product is postulated to be due to the hydrolysis of the ester. Confirmation of the O-alkylation was obtained by synthesizing the [F-19]fluoromethyl(tert-butoxycarbonyl)-Ltryptophanate insitu and examining its NMR characteristics using multiple NMR techniques. Similar results were also obtained when reacting Boc-tryptophan-N-carboxyanhydride precursor with fluoromethyl tosylate.
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