Rearrangement with formamide extrusion in the electrospray mass spectra of aminoacylbenzylamines.
Several aminoacylbenzylamines and their analogs were synthesized and analyzed by electrospray ionization mass spectrometry together with high-resolution and tandem mass spectrometric techniques. Fragment ions ([M + H - CH3NO](+)) were observed and attributed to a transfer of the benzyl group to the N-terminal amino group, leading to elimination of formamide. The proposed mechanism is supported by accurate mass measurements, and by experiments on deuterium labeling and variations of functional groups.
Chen
J
J
The Key Laboratory for Bioorganic Phosphorus Chemistry, Ministry of Education, Department of Chemistry, School of Life Sciences and Engineering, Tsinghua University, Beijing 100084, P. R. China.
Jiang
Y
Y
Fu
H
H
Chen
Y
Y
Cheng
C
C
Zhao
Y
Y
D000596:Amino Acids / Q000032:analysis*; D001596:Benzylamines / Q000737:chemistry*; D005559:Formamides; D013058:Mass Spectrometry / Q000379:methods; D008968:Molecular Conformation; D015394:Molecular Structure; D021241:Spectrometry, Mass, Electrospray Ionization / Q000379:methods
D000596:Amino Acids; D001596:Benzylamines; D005559:Formamides; C031066:formamide