Valence anions of N-acetylproline in the gas phase: computational and anion photoelectron spectroscopic studies.

Content Provider	Europe PMC
Author	Chomicz, Lidia Rak, Janusz Paneth, Piotr Sevilla, Michael Ko, Yeon Jae Wang, Haopeng Bowen, Kit H.
Copyright Year	2011
Abstract	We report the photoelectron spectrum of anionic N-acetylproline, (N-AcPro)−, measured with 3.49 eV photons. This spectrum, which consists of a band centered at an electron binding energy of 1.4 eV and a higher energy spectral tail, confirms that N-acetylproline forms a valence anion in the gas phase. The neutrals and anions of N-AcPro were also studied computationally at the B3LYP/6-31++G(d,p) level. Based on the calculations, we conclude that the photoelectron spectrum is due to anions which originated from proton transfer induced by electron attachment to the π* orbital localized at the acetyl group of N-AcPro. We also characterized the energetics of reaction paths leading to pyrrolidine ring opening in the anionic N-AcPro. These data suggest that electron induced decomposition of peptides/proteins comprising proline strongly depends on the presence of proton donors in the close vicinity to the proline residue.
Related Links	https://europepmc.org/backend/ptpmcrender.fcgi?accid=PMC3298562&blobtype=pdf
ISSN	00219606
Volume Number	135
DOI	10.1063/1.3625957
PubMed Central reference number	PMC3298562
Issue Number	11
PubMed reference number	21950856
Journal	The Journal of Chemical Physics [J Chem Phys]
e-ISSN	10897690
Language	English
Publisher	American Institute of Physics
Publisher Date	2011-09-01
Access Restriction	Open
Rights License	Copyright © 2011 American Institute of Physics
Content Type	Text
Resource Type	Article
Subject	Physics and Astronomy Medicine Physical and Theoretical Chemistry