Rapid radiosynthesis of [11C] and [14C]azelaic, suberic, and sebacic acids for in vivo mechanistic studies of systemic acquired resistance in plants
✍ Scribed by Marcel Best; Andrew N. Gifford; Sung Won Kim; Ben Babst; Markus Piel; Frank Rösch; Joanna S. Fowler
- Publisher
- John Wiley and Sons
- Year
- 2011
- Tongue
- French
- Weight
- 174 KB
- Volume
- 55
- Category
- Article
- ISSN
- 0022-2135
No coin nor oath required. For personal study only.
✦ Synopsis
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.