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Analysis by fast atom bombardment mass spectrometry of 4,4‐dicarboxy‐5‐(pyridoxyl‐5′‐phosphate)‐proline, of 4‐carboxy‐5‐(pyridoxyl‐5′‐phosphate)‐proline and 4,4‐dicarboxy‐5‐pyridoxylproline
Author(s) -
Capasso R.,
Pucci P.,
Randazzo G.,
Ritieni A.,
Malorni A.
Publication year - 1989
Publication title -
biomedical and environmental mass spectrometry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.475
H-Index - 121
eISSN - 1096-9888
pISSN - 0887-6134
DOI - 10.1002/bms.1200181107
Subject(s) - proline , phosphate , chemistry , fast atom bombardment , mass spectrometry , chromatography , organic chemistry , biochemistry , amino acid
γ‐Carboxyglutamic acid (Gla) reacts easily and quantitatively with piridoxal‐5′‐phosphate in H 2 O at room temperature, to give the 4,4‐dicarboxy‐5‐(pyridoxyl‐5′‐phosphate)‐proline (1). This product has been characterized by fast atom bombardment (FAB) mass spectrometry, including the B/E linked scan technique, ultraviolet and 1 H nuclear magnetic resonance (NMR) analysis. In order to support further on the structure of 1, the 4‐monodecarboxyderivative (2), obtained by heating compound 1 at 100°C for 30 min and the 5′‐dephosphoderivative (3), obtained by enzymatic hydrolysis of 1 with alkaline phosphatase, were also analysed by FAB and 1 H NMR techniques. FAB was shown to be the only adequate ionization technique to deal with such thermolabile and non‐volatile compounds and could provide an elegant and fast method to detect Gla in biological matrices.