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  • Title: Characterization of cationic glycoporphyrins by electrospray tandem mass spectrometry.
    Author: Silva EM, Serra VV, Ribeiro AO, Tomé JP, Domingues P, Faustino MA, Neves MG, Tomé AC, Cavaleiro JA, Ferrer-Correia AJ, Iamamoto Y, Domingues MR.
    Journal: Rapid Commun Mass Spectrom; 2006; 20(23):3605-11. PubMed ID: 17091537.
    Abstract:
    Novel cationic porphyrin derivatives having a galactose or a bis(isopropylidene)galactose unit linked directly to a pyridine or to an aminophenyl group were characterized by electrospray tandem mass spectrometry (ESI-MS/MS). The electrospray mass spectra (ESI-MS) show the M(+) ions, since these porphyrins are already monocharged in solution. The fragmentation of these ions under ESI-MS/MS conditions was studied and it was found that elimination of the sugar residue as a radical (-163 or -243 Da) is a common fragmentation pathway. Loss of the sugar unit as a neutral fragment (-162 or -242 Da) and cross-ring fragmentations typical of glyco-derivatives are also observed for the pyridinium glycoporphyrins, but they are absent in the case of ammonium glycoporphyrins. The cationic beta-pyridiniumvinyl porphyrins show an atypical fragmentation due to the cleavage of the C(5)-C(6) bond of the sugar unit. Overall, the different patterns of fragmentation observed in the ESI-MS/MS spectra of the sugar pyridinium porphyrins and of the sugar ammonium phenyl porphyrins can give important information about the type of spacer between the porphyrin and the sugar unit.
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