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Matrix‐assisted laser desorption/ionization time‐of‐flight and nano‐electrospray ionization ion trap mass spectrometric characterization of 1‐cyano‐2‐substituted‐benz[ f ]isoindole derivatives of peptides for fluorescence detection
Author(s) -
Linnemayr K.,
Brückner A.,
Körner R.,
Hahn R.,
Jungbauer A.,
Josic Dj.,
Roepstorff P.,
Rizzi A.,
Allmaier G.
Publication year - 1999
Publication title -
journal of mass spectrometry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.475
H-Index - 121
eISSN - 1096-9888
pISSN - 1076-5174
DOI - 10.1002/(sici)1096-9888(199904)34:4<427::aid-jms779>3.0.co;2-c
Subject(s) - chemistry , fragmentation (computing) , mass spectrometry , electrospray ionization , quadrupole ion trap , ion , ion trap , electrospray , tandem mass spectrometry , peptide , analytical chemistry (journal) , ionization , dissociation (chemistry) , matrix assisted laser desorption/ionization , desorption , photochemistry , chromatography , organic chemistry , biochemistry , adsorption , computer science , operating system
A series of hexa‐ to decapeptides (molecular mass range800–1200) were labeled withnaphthalene‐2,3‐dicarboxaldehyde, which preferentiallyreacts with the primary amino groups of a peptide. A highly stablepeptide conjugate is formed, which allows selective analysis byfluorescence at excitation and emission wavelengths of 420 and 490nm, respectively. After removal of unreacted compounds, the peptideconjugates were characterized by matrix‐assisted laserdesorption/ionization (MALDI)time‐of‐flight and nano‐electrospray ionization(ESI) ion trap mass spectrometry. They readily form both[M+H] + ions by MALDI and both[M+H] + and [M+2H] 2+ ions by ESI. Furthermore, the fragmentationbehavior of the N‐terminally tagged peptides, exhibiting anuncharged N‐terminus, was investigated applyingpost‐source decay fragmentation with a curved field reflectorand collision‐induced dissociation with a quadrupole ion trap.Fragmentation is dominated in both cases by series of a‐,b‐ and y‐type ions and [M+H−HCN] + ions. Peptide bonds adjacent to the fluorescencelabel were less susceptible to cleavage than the bonds of thenon‐derivatized peptide ions. In general, the resultingfragment ion patterns were less complex than those of theunderivatized peptides. Copyright © 1999 John Wiley & Sons,Ltd.