Characterization of Stereoisomeric α-Methylene-γ-lactone Furanosidic Derivatives by Direct Chemical Ionization Mass Spectrometry and Liquid Secondary Ion Mass Spectrometry with Tandem Mass Spectrometry

Abstract

Several furanosidic derivatives have been found to have biological activity and have been used both as fungicides and plant growth regulators. In particular, those carbohydrate derivatives that contain the α-methylene-γ-lactone unit have interesting potential applications. The present study deals with the mass spectrometric characterization of furanosidic compounds having a α-methylene-γ-lactone unit, using different ionization techniques: chemical ionization mass spectrometry and liquid secondary ion mass spectrometry together with metastable ion analysis and high-energy collision-induced dissociation. The objective of this study was to determine the influence on the respective fragmentation patterns of structural differences present in the stereoisomers. Common fragmentation differences relate to the extent of the loss of water which occurs together with the loss of acetone and to the formation of C7H7+ ions.