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- W1983963095 abstract "The dissociative behavior of peptide amides and free acids was explored using low-energy collision-induced dissociation and high level computational theory. Both positive and negative ion modes were utilized, but the most profound differences were observed for the deprotonated species. Deprotonated peptide amides produce a characteristic c(m-2)(-) product ion (where m is the number of residues in the peptide) that is either absent or in low abundance in the analogous peptide acid spectrum. Peptide acids show an enhanced formation of c(m-3)(-); however, this is not generally as pronounced as c(m-2)(-) production from amides. The most notable occurrence of an amide-specific product ion is for laminin amide (YIGSR-NH(2)) and this case was investigated using several modified peptides. Mechanisms involving 6- and 9-membered ring formation were proposed, and their energetic properties were investigated using G3(MP2) molecular orbital theory calculations. For example, with C-terminal deprotonation of pentaglycine amide, formation of c(m-2)(-) and a 6-membered ring diketopiperazine neutral requires >31.6 kcal/mol, which is 26.1 kcal/mol less than the analogous process involving the peptide acid. The end group specific fragmentation of peptide amides in the negative ion mode may be useful for identifying such groups in proteomic applications." @default.
- W1983963095 created "2016-06-24" @default.
- W1983963095 creator A5049159400 @default.
- W1983963095 creator A5077080834 @default.
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- W1983963095 creator A5090755424 @default.
- W1983963095 date "2012-07-26" @default.
- W1983963095 modified "2023-10-11" @default.
- W1983963095 title "A Comparison of the Effects of Amide and Acid Groups at the C-Terminus on the Collision-Induced Dissociation of Deprotonated Peptides" @default.
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- W1983963095 doi "https://doi.org/10.1007/s13361-012-0431-x" @default.
- W1983963095 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/22833234" @default.
- W1983963095 hasPublicationYear "2012" @default.
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