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Fragmentation pathways of eight nitrogen-containing bisphosphonates (BPs) investigated by ESI-MSn in negative ion mode by Zhibo Qu; Xiaolan Chen; Chen Qu; Lingbo Qu; Jinwei Yuan; Donghui Wei; Huina Li; Xiaoying Huang; Yuqin Jiang; Yufen Zhao is a Chemistry article available to read on EtoBox.

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Fragmentation pathways of eight nitrogen-containing bisphosphonates (BPs), including Pamidronate, Alendronate, and five corresponding acylated derivatives, and Risedronate, were investigated by electrospray ionization mass spectrometry (ESI-MS) in conjunction with tandem mass spectrometry in negative ion mode. Characteristic fragment ions involved were formed by successive loss of water molecules, including ␣, ␤-unsaturated product ions formed by dehydration of the ␣-hydroxyl group and ␤-hydrogen, cyclic ions with P-O-P four-membered rings formed by dehydration of the two -OH groups attached to two phosphorus atoms, and cyclic phosphoramide ions with five-or six-membered rings formed by loss of water via an intramolecular nucleophilic substitution reaction, in which -NH 2 (or -NH-) group on ␥ or ␦ carbon acted as the nucleophile to attack phosphorus atom of P O group at the initial stage. Another notable characteristic product ion [HP 2 O 5 ] -at m/z 143, shown by all eight ESI-MS 2 spectra, is a diagnostic ion of bisphosphonate group, formed from the four-membered ring ion containing P-O-P. Some additional fragmentation ions were produced from chloroacetyl Alendronate, chloroacety

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Author

Zhibo Qu; Xiaolan Chen; Chen Qu; Lingbo Qu; Jinwei Yuan; Donghui Wei; Huina Li; Xiaoying Huang; Yuqin Jiang; Yufen Zhao

Publisher

Elsevier Science; Elsevier ; Elsevier BV (ISSN 1387-3806)

Published

2010

Language

EN

Field

Chemistry (Physical Sciences)