Amide bond dissociation in protonated peptides. Structures of the N-terminal ionic and neutral fragments

被引:162
作者
Nold, MJ
Wesdemiotis, C
Yalcin, T
Harrison, AG
机构
[1] UNIV AKRON,DEPT CHEM,AKRON,OH 44325
[2] UNIV TORONTO,DEPT CHEM,TORONTO,ON M5S 3H6,CANADA
来源
INTERNATIONAL JOURNAL OF MASS SPECTROMETRY AND ION PROCESSES | 1997年 / 164卷 / 1-2期
关键词
protonated peptides; peptide bond dissociation; N-terminal fragments; oxazolones; diketopiperazines; MS3; neutral fragment reionization;
D O I
10.1016/S0168-1176(97)00044-X
中图分类号
O64 [物理化学(理论化学)、化学物理学]; O56 [分子物理学、原子物理学];
学科分类号
070203 ; 070304 ; 081704 ; 1406 ;
摘要
Three-stage tandem mass spectrometry (MS3) and neutral fragment reionization (NfR) are utilized to investigate the structures of the N-terminal ionic (b(i)) and neutral backbone fragments, respectively, produced from break-up of the amide bond in protonated peptides that have been collisionally activated. The b-type ion from [M + H](+) of C6H5CO-GF, which is produced by loss of the C-terminal phenylalanine, has the structure of protonated 2-phenyl-5-oxazolone. Conversely, the neutral fragment accompanying the y-type ion (protonated phenylalanine) is 2-phenyl-5-oxazolone. The b(2) ions arising from [M + H](+) of underivatized tripeptides are also found to be protonated oxazolones. On the other hand, the neutral fragments released from the N-terminus of the tripeptides upon formation of y(1) are shown to be diketopiperazines and not oxazolones. The combined MS3 and NfR data help propose dissociation mechanisms that account for the observed structures of ionic and neutral backbone fragments. (C) 1997 Elsevier Science B.V.
引用
收藏
页码:137 / 153
页数:17
相关论文
共 55 条
[1]  
Ambihapathy K, 1997, J MASS SPECTROM, V32, P209, DOI 10.1002/(SICI)1096-9888(199702)32:2<209::AID-JMS466>3.3.CO
[2]  
2-3
[3]  
AUBAGNAC JL, 1985, ORG MASS SPECTROM, V20, P428
[4]  
Banks JF, 1996, METHOD ENZYMOL, V270, P486
[5]   FAST ATOM BOMBARDMENT OF SOLIDS (FAB) - A NEW ION-SOURCE FOR MASS-SPECTROMETRY [J].
BARBER, M ;
BORDOLI, RS ;
SEDGWICK, RD ;
TYLER, AN .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1981, (07) :325-327
[6]  
Beavis RC, 1996, METHOD ENZYMOL, V270, P519
[7]  
Benson S.W., 1968, THERMOCHEMICAL KINET
[8]   UNIMOLECULAR CHEMISTRY OF PROTONATED GLYCINE AND ITS NEUTRALIZED FORM IN THE GAS-PHASE [J].
BERANOVA, S ;
CAI, J ;
WESDEMIOTIS, C .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (37) :9492-9501
[9]   CHARACTERIZATION BY TANDEM MASS-SPECTROMETRY OF STRUCTURAL MODIFICATIONS IN PROTEINS [J].
BIEMANN, K ;
SCOBLE, HA .
SCIENCE, 1987, 237 (4818) :992-998
[10]   SEQUENCING OF PEPTIDES BY TANDEM MASS-SPECTROMETRY AND HIGH-ENERGY COLLISION-INDUCED DISSOCIATION [J].
BIEMANN, K .
METHODS IN ENZYMOLOGY, 1990, 193 :455-479