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Characterization of impurities in a synthetic renin substrate peptide by fast‐atom bombardment mass spectrometry and hybrid tandem mass spectrometry
Author(s) -
Mathews W. Rodney,
Runge Thomas A.,
Haroldsen Peter E.,
Gaskell Simon J.,
Tomer K. B.
Publication year - 1989
Publication title -
rapid communications in mass spectrometry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.528
H-Index - 136
eISSN - 1097-0231
pISSN - 0951-4198
DOI - 10.1002/rcm.1290030912
Subject(s) - chemistry , fast atom bombardment , tandem mass spectrometry , mass spectrometry , isobaric labeling , yield (engineering) , derivatization , substrate (aquarium) , protein mass spectrometry , peptide , tandem mass tag , chromatography , combinatorial chemistry , proteomics , biochemistry , materials science , oceanography , metallurgy , geology , quantitative proteomics , gene
Fast‐atom bombardment mass spectrometry of a synthetic renin substrate decapeptide (Pro‐His‐Pro‐Phe‐His‐Leu‐Val‐Ile‐His‐ D ‐Lys) indicated the presence of several of side‐products, including a component 12 Da higher in mass. Low‐energy collisionally activated decomposition analyses were performed using a hybrid tanden, instrument and demonstrated that the heavier side product had two components, in which the structural modification was either at the N‐ or the C‐terminus. Additional analyses of the N ‐acetyl derivative indicated that for each component the strucutrual modification blcoked a site of N ‐acetylation. It is suggested that the formation of these side products is attributable to the generation of formaldehyde, during removal of the histidine protecting group (benzyloxymethyl), which reacts with the N‐terminus of the peptide to give an imidazolidinone structure or with the D ‐lysine ε‐amine group to yield an imine. While the precise genesis of the side‐products remains speculative, it is clear that the combined strategy of derivatization and tandem mass spectrometry has allowed structural conclusions concerning individual components of an isobaric mixture.