Synthesis of 13 C-labelled cutin and suberin monomeric dicarboxylic acids of the general formula HO213 C-(CH2 )n -13 CO2 H (n = 10, 12, 14, 16, 18, 20, 22, 24, 26, 28).

Abstract

13 C-labeled dicarboxylic acids HO213 C-(CH2 )n -13 CO2 H (n = 10, 12, 14, 16, 18, 20, 22, 24, 26, 28) have been synthesized as internal standards for LC-MS and GC-MS analysis of cutin and suberin monomer degradation by soil-based microorganisms. Different synthetic strategies had to be applied depending on the chain length of the respective synthetic target and because of economic considerations. 13 C-labels were introduced by nucleophilic substitution of a suitable leaving group with labelled potassium cyanide and subsequent hydrolysis of the nitriles to produce the corresponding dicarboxylic acids. All new compounds are characterized by GC/MS, IR, and NMR methods as well as by elemental analysis.