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Peptide Bond Tautomerization Induced by Divalent Metal Ions: Characterization of the Iminol Configuration
Author(s) -
Dunbar Robert C.,
Steill Jeffrey D.,
Polfer Nicolas C.,
Berden Giel,
Oomens Jos
Publication year - 2012
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201200437
Subject(s) - tautomer , chemistry , dipeptide , infrared multiphoton dissociation , solvation , ion , divalent , dissociation (chemistry) , metal ions in aqueous solution , crystallography , infrared spectroscopy , stereochemistry , peptide , photochemistry , organic chemistry , biochemistry
Rearranged : The attachment of gas‐phase divalent metal ions that bind as strongly as Mg 2+ and transition‐metal ions to the dipeptide PhePhe results in displacement of the amide proton by the newly characterized iminol tautomerization rearrangment. More weakly coordinating ions bind in the known charge‐solvation mode. Infrared multiple‐photon dissociation spectroscopy using the free‐electron laser clearly shows the tautomeric transition.