| Electrospray tandem mass spectrometry of new porphyrin amino acid conjugates. | |
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MedLine Citation:
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PMID: 16106376 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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Porphyrin amino acid conjugates with one or two porphyrin units were analyzed by electrospray ionization tandem mass spectrometry (ESI-MS/MS). The ESI-MS spectra of all the porphyrins studied, obtained in positive ion mode, show the presence of the corresponding protonated molecule [M+H]+; ESI-MS spectra of diporphyrinyl compounds also show the doubly charged ions [M+2H]2+. The fragmentations of these ions induced by collision with argon were studied (ESI-MS/MS). ESI-MS/MS gives detailed structural information about the amino acids associated with the porphyrin. Cleavage of the bonds in the vicinity of the porphyrin moiety and those involving the side chain of amino acid residues gives structural information about this type of association. A fragmentation common to all derivatives corresponds to the cleavage of the phenyl-CO bond. The expected cleavage of the amide bond, that links the porphyrin to the amino acid moiety, is a minor fragmentation, which in some cases is even absent. The MS/MS spectra of the monoporphyrinyl derivatives show product ions characteristic of the amino acid linked to the porphyrin; the fragmentation also indicates when the amino acids has a terminal carboxylic group or a terminal ester group. The fragmentations of the diporphyrinyl compounds occur mainly by the cleavage of the spacer, leading, in the case of the doubly charged ions, to predominantly mono-charged ions, indicating a preferential location of the two protons in separated porphyrinic units. |
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Authors:
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V Vaz Serra; M R M Domingues; M A F Faustino; P Domingues; J P C Tomé; M G P M S Neves; A C Tomé; J A S Cavaleiro; A J Ferrer-Correia |
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Publication Detail:
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Type: Journal Article; Research Support, Non-U.S. Gov't |
Journal Detail:
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Title: Rapid communications in mass spectrometry : RCM Volume: 19 ISSN: 0951-4198 ISO Abbreviation: Rapid Commun. Mass Spectrom. Publication Date: 2005 |
Date Detail:
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Created Date: 2005-09-05 Completed Date: 2006-03-02 Revised Date: 2006-11-15 |
Medline Journal Info:
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Nlm Unique ID: 8802365 Medline TA: Rapid Commun Mass Spectrom Country: England |
Other Details:
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Languages: eng Pagination: 2569-80 Citation Subset: IM |
Copyright Information:
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Copyright (c) 2005 John Wiley & Sons, Ltd. |
Affiliation:
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Department of Chemistry, University of Aveiro, 3810-193 Aveiro, Portugal. |
Export Citation:
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APA/MLA Format Download EndNote Download BibTex |
| MeSH Terms | |
Descriptor/Qualifier:
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Amino Acids
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chemistry* Molecular Structure Porphyrins / chemistry* Spectrometry, Mass, Electrospray Ionization Structure-Activity Relationship |
| Chemical | |
Reg. No./Substance:
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0/Amino Acids; 0/Porphyrins |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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