Premium
Rapid radiosynthesis of [ 11 C] and [ 14 C]azelaic, suberic, and sebacic acids for in vivo mechanistic studies of systemic acquired resistance in plants
Author(s) -
Best Marcel,
Gifford Andrew N.,
Kim Sung Won,
Babst Ben,
Piel Markus,
Rösch Frank,
Fowler Joanna S.
Publication year - 2012
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.1951
Subject(s) - azelaic acid , sebacic acid , chemistry , dicarboxylic acid , potassium cyanide , nuclear chemistry , organic chemistry , radiosynthesis , stereochemistry , cyanide , in vivo , microbiology and biotechnology , biology
A recent report that the aliphatic dicarboxylic acid, azelaic acid (1,9‐nonanedioic acid) but not related acids, suberic acid (1,8‐octanedioic acid) or sebacic (1,10‐decanedioic acid) acid induces systemic acquired resistance to invading pathogens in plants stimulated the development of a rapid method for labeling these dicarboxylic acids with 11 C and 14 C for in vivo mechanistic studies in whole plants. 11 C‐labeling was performed by reaction of ammonium [ 11 C]cyanide with the corresponding bromonitrile precursor followed by hydrolysis with aqueous sodium hydroxide solution. Total synthesis time was 60 min. Median decay‐corrected radiochemical yield for [ 11 C]azelaic acid was 40% relative to trapped [ 11 C]cyanide, and specific activity was 15 GBq/µmol. Yields for [ 11 C]suberic and sebacic acids were similar. The 14 C‐labeled version of azelaic acid was prepared from potassium [ 14 C]cyanide in 45% overall radiochemical yield. Radiolabeling procedures were verified using 13 C‐labeling coupled with 13 C‐NMR and liquid chromatography–mass spectrometry analysis. The 11 C and 14 C‐labeled azelaic acid and related dicarboxylic acids are expected to be of value in understanding the mode‐of‐action, transport, and fate of this putative signaling molecule in plants. Copyright © 2011 John Wiley & Sons, Ltd.