Synthesis of the phytohormone [11C]methyl jasmonate via methylation on a C18 Sep Pak™ cartridge

TY - JOUR

T1 - Synthesis of the phytohormone [11C]methyl jasmonate via methylation on a C18 Sep Pak™ cartridge

AU - Herth, Matthias M.

AU - Thorpe, Michael R.

AU - Ferrieri, Richard A.

PY - 2005/4/1

Y1 - 2005/4/1

N2 - [11C]labeled (±)-methyl jasmonate was synthesized using a C18 Sep Pak™ at ∼100°C to sustain a solid-supported 11C-methylation reaction of sodium (±)-jasmonate using [ 11C]methyl iodide. After reaction, the Sep Pak was rinsed with acetone to elute the labeled product, and the solvent evaporated rendering [11C]-(+)-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 [11C]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 10mCi of purified radiotracer. A specific activity of 0.5 Ci/μmol was achieved using a short 3 min cyclotron beam to produce the starting 11C.

AB - [11C]labeled (±)-methyl jasmonate was synthesized using a C18 Sep Pak™ at ∼100°C to sustain a solid-supported 11C-methylation reaction of sodium (±)-jasmonate using [ 11C]methyl iodide. After reaction, the Sep Pak was rinsed with acetone to elute the labeled product, and the solvent evaporated rendering [11C]-(+)-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 [11C]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 10mCi of purified radiotracer. A specific activity of 0.5 Ci/μmol was achieved using a short 3 min cyclotron beam to produce the starting 11C.

KW - C-labeled phytohormone

KW - [C]methyl jasmonate

KW - Solid-supported C-methylation

UR - http://www.scopus.com/inward/record.url?scp=17844398236&partnerID=8YFLogxK

U2 - 10.1002/jlcr.933

DO - 10.1002/jlcr.933

M3 - Journal article

AN - SCOPUS:17844398236

SN - 0362-4803

VL - 48

SP - 379

EP - 386

JO - Journal of Labelled Compounds and Radiopharmaceuticals

JF - Journal of Labelled Compounds and Radiopharmaceuticals

IS - 5

ER -