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Defying Entropy: Forming Large Head‐to‐Tail Macrocycles in the Gas Phase
Author(s) -
Tirado Marcus,
Polfer Nicolas C.
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.201202405
Subject(s) - oxazolone , isomerization , protonation , infrared multiphoton dissociation , gas phase , chemistry , dissociation (chemistry) , infrared spectroscopy , stereochemistry , crystallography , ion , computer science , organic chemistry , catalysis
Spectral fingerprints : Collision‐induced dissociation (CID) of protonated peptides in the gas phase results in linear fragment ions with a five‐membered oxazolone ring on their C‐terminal side. Infrared spectroscopy confirms that smaller fragments adopt oxazolone structures. Conversely, in mid‐sized and larger fragments an isomerization to “head‐to‐tail” macrocycles is observed (see picture).