Fragmentation pattern of amides by EI and HRESI: study of protonation sites using DFT-3LYP data.

ABSTRACT: Amides are important natural products which occur in a few plant families. Piplartine and piperine, major amides in Piper tuberculatum and P. nigrum, respectively, have shown a typical N-CO cleavage when analyzed by EI-MS or HRESI-MS. In this study several synthetic analogs of piplartine and piperine were subjected to both types of mass spectrometric analysis in order to identify structural features influencing fragmentation. Most of the amides showed an intense signal of the protonated molecule [M + H]⁺ when subjected to both HRESI-MS and EI-MS conditions, with a common outcome being the cleavage of the amide bond (N-CO). This results in the loss of the neutral amine or lactam and the formation of aryl acylium cations. The mechanism of N-CO bond cleavage persists

SUBMITTER: Fokoue HH 

PROVIDER: S-EPMC9080946 | biostudies-literature | 2018 Jun

REPOSITORIES: biostudies-literature