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

Matthias M. Herth; Michael R. Thorpe; Richard A. Ferrieri

doi:10.1002/jlcr.933

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

Matthias M. Herth, Michael R. Thorpe, Richard A. Ferrieri^*

^*Corresponding author for this work

7 Citations (Scopus)

Abstract

[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.

Original language	English
Journal	Journal of Labelled Compounds and Radiopharmaceuticals
Volume	48
Issue number	5
Pages (from-to)	379-386
Number of pages	8
ISSN	0362-4803
DOIs	https://doi.org/10.1002/jlcr.933
Publication status	Published - 1 Apr 2005

Keywords

C-labeled phytohormone
[C]methyl jasmonate
Solid-supported C-methylation

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title = "Synthesis of the phytohormone [11C]methyl jasmonate via methylation on a C18 Sep Pak{\texttrademark} cartridge",

abstract = "[11C]labeled (±)-methyl jasmonate was synthesized using a C18 Sep Pak{\texttrademark} 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.",

keywords = "C-labeled phytohormone, [C]methyl jasmonate, Solid-supported C-methylation",

author = "Herth, {Matthias M.} and Thorpe, {Michael R.} and Ferrieri, {Richard A.}",

year = "2005",

month = apr,

day = "1",

doi = "10.1002/jlcr.933",

language = "English",

volume = "48",

pages = "379--386",

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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

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DO - 10.1002/jlcr.933

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AN - SCOPUS:17844398236

SN - 0362-4803

VL - 48

SP - 379

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JO - Journal of Labelled Compounds and Radiopharmaceuticals

JF - Journal of Labelled Compounds and Radiopharmaceuticals

IS - 5

ER -

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

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