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Synthesis of the phytohormone [ 11 C]methyl jasmonate via methylation on a C 18 Sep Pak™ cartridge
Author(s) -
Herth Matthias M.,
Thorpe Michael R.,
Ferrieri Richard A.
Publication year - 2005
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.933
Subject(s) - chemistry , methyl jasmonate , methyl iodide , jasmonic acid , acetone , jasmonate , nuclear chemistry , chromatography , radiochemistry , organic chemistry , salicylic acid , biochemistry , gene , arabidopsis , mutant
[ 11 C]labeled (±)‐methyl jasmonate was synthesized using a C 18 Sep Pak™ at ∼100°C to sustain a solid‐supported 11 C‐methylation reaction of sodium (±)‐jasmonate using [ 11 C]methyl iodide. After reaction, the Sep Pak was rinsed with acetone to elute the labeled product, and the solvent evaporated rendering [ 11 C]‐(±)‐methyl jasmonate at 96% radiochemical purity. The substrate, (±)‐jasmonic acid, was retained on the Sep Pak so further chromatography was unnecessary. Total synthesis time was 25 min from the end of bombardment (EOB) which included 15 min to generate [ 11 C]methyl iodide using the GE Medical Systems PET Trace MeI system, 5 min for reaction and extraction from the cartridge, and 5 min to reformulate the product for plant administration. An overall radiochemical yield (at EOB) of 17±4.3% was obtained by this process, typically producing 10 mCi of purified radiotracer. A specific activity of 0.5 Ci/µmol was achieved using a short 3 min cyclotron beam to produce the starting 11 C. Copyright © 2005 John Wiley & Sons, Ltd.