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Effect of metal cationization on the tandem mass spectra of glycosyl dithioacetals

✍ Scribed by K. P. Madhusudanan; Brijesh Kumar; Pallavi Tiwari; Soni Kamlesh Madhusudan; A. K. Misra

Publisher
John Wiley and Sons
Year
2005
Tongue
English
Weight
303 KB
Volume
40
Category
Article
ISSN
1076-5174

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✦ Synopsis

Abstract

The effect of metal cationization on the tandem mass spectra of glycosyl dithioacetals of glucose, mannose, galactose, rhamnose, arabinose and xylose was studied by electrospray ionization mass spectrometry under ammonium and metal (Li, Na, Ag and Cu) ion cationization conditions. The ammonium‐cationized glycosyl dithioacetals fragment by loss of ammonia followed by either two molecules of EtSH or one molecule of EtSH and one molecule of H~2~O. Lithium cationization leads to additional eliminations such as EtSEt and EtSSEt and Cο£ΏC cleavages. Elimination of EtSH is not observed under sodium cationization. Silver cationization, on the other hand, leads to additional fragmentations involving the elimination of silver as AgOH and AgSEt. Copper cationization results in adducts where copper has undergone a change of oxidation state from II to I. Li^+^, Ag^+^ and Cu^+^ cationization seem to favour cyclization resulting in elimination of EtSH. However, the mechanisms seem to be differently affected by different metal ions. Li^+^ and Ag^+^ cationization appear to be non‐specific and favour cyclization involving C2‐, C4‐ and C5‐hydroxyl hydrogens, whereas Cu^+^ cationization seems to favour cyclization involving C4‐hydroxyl hydrogen. Copyright Β© 2004 John Wiley & Sons, Ltd.

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