Collision-induced dissociation mass spectra of glucosinolate anions

✍ Scribed by Jason B. Bialecki; Josef Ruzicka; Carl S. Weisbecker; Meena Haribal; Athula B. Attygalle

• Publisher: John Wiley and Sons
• Year: 2010
• Tongue: English
• Weight: 608 KB
• Volume: 45
• Category: Article
• ISSN: 1076-5174
• DOI: 10.1002/jms.1711

✦ Synopsis

Abstract

Collision‐induced dissociation (CID) mass spectra of differently substituted glucosinolates were investigated under negative‐ion mode. Data obtained from several glucosinolates and their isotopologues (^34^S and ^2^H) revealed that many peaks observed are independent of the nature of the substituent group. For example, all investigated glucosinolate anions fragment to produce a product ion observed at m/z 195 for the thioglucose anion, which further dissociates via an ion/neutral complex to give two peaks at m/z 75 and 119. The other product ions observed at m/z 80, 96 and 97 are characteristic for the sulfate moiety. The peaks at m/z 259 and 275 have been attributed previously to glucose 1‐sulfate anion and 1‐thioglucose 2‐sulfate anion, respectively. However, based on our tandem mass spectrometric experiments, we propose that the peak at m/z 275 represents the glucose 1‐thiosulfate anion. In addition to the common peaks, the spectrum of phenyl glucosinolate (β‐D‐Glucopyranose, 1‐thio‐, 1‐[N‐(sulfooxy)benzenecarboximidate] shows a substituent‐group‐specific peak at m/z 152 for C~6~H~5~‐C(NOH)S^−^, the CID spectrum of which was indistinguishable from that of the anion of synthetic benzothiohydroxamic acid. Similarly, the m/z 201 peak in the spectrum of phenyl glucosinolate was attributed to C~6~H~5~‐C(S)OSO~2~^−^. Copyright © 2009 John Wiley & Sons, Ltd.