TY - JOUR
T1 - Collision-induced dissociation mass spectra of glucosinolate anions
AU - Bialecki, Jason B.
AU - Ruzicka, Josef
AU - Weisbecker, Carl S.
AU - Haribal, Meena
AU - Attygalle, Athula B.
PY - 2010/3
Y1 - 2010/3
N2 - Collision-induced dissociation (CID)mass spectra of differently substituted glucosinolates were investigated under negative-ion mode. Data obtained from several glucosinolates and their isotopologues (34S and 2H) 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 atm/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 C6H5-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 C6H5-C(=S)OSO2-.
AB - Collision-induced dissociation (CID)mass spectra of differently substituted glucosinolates were investigated under negative-ion mode. Data obtained from several glucosinolates and their isotopologues (34S and 2H) 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 atm/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 C6H5-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 C6H5-C(=S)OSO2-.
KW - Collision-induced dissociation
KW - Deuterium-labeled compounds
KW - Even-electron ions
KW - Fragmentation
KW - Glucosinolates
KW - Isotopologues
KW - Negative ions
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U2 - 10.1002/jms.1711
DO - 10.1002/jms.1711
M3 - Article
C2 - 20033929
AN - SCOPUS:77749267765
SN - 1076-5174
VL - 45
SP - 272
EP - 283
JO - Journal of Mass Spectrometry
JF - Journal of Mass Spectrometry
IS - 3
ER -