Ion mobility experiments are combined with Infra-Red Multiple Photon Dissociation (IRMPD) spectroscopy and quantum chemical calculations for assessing the role of chirality in the structure of protonated and sodiated di- or tetra-peptides. Sodiated systems show a strong chirality dependence of the competition between Na(+)O and Na(+)π interactions. Chirality effects are more subtle in protonated systems and manifest themselves by differences in the secondary interactions such hydrogen bonds between neutral groups or those involving the aromatic rings.

Download full-text PDF

Source
http://dx.doi.org/10.1039/c5cp06768eDOI Listing

Publication Analysis

Top Keywords

protonated sodiated
8
ion mobility
8
chirality-dependent structuration
4
structuration protonated
4
sodiated polyphenylalanines
4
polyphenylalanines irmpd
4
irmpd ion
4
mobility studies
4
studies ion
4
mobility experiments
4

Similar Publications

In our previous work, the sodiation of melittin, cytochrome c, and ubiquitin in a 1 mM NaOH water/methanol solution was studied by electrospray mass spectrometry. It was suggested that the α-helix is more resistant to sodiation than the β-sheet. In this study, sodiation of enhanced green fluorescent protein (EGFP) composed of a β-barrel was studied in 1% CHCOOH (AcOH) or 1 mM NaOH water/methanol solution by electrospray mass spectrometry.

View Article and Find Full Text PDF

Charge-solvated versus protonated salt forms of cyclodepsipeptide toxins in electrospray: Dissociation of alkali-cationized forms enables straightforward sequencing of cereulide.

J Mass Spectrom

June 2024

Université Paris Saclay, CEA-INRAE, Laboratoire Innovations en Spectrométrie de Masse pour la Santé (LI-MS), DRF/Institut Joliot/DMTS/SPI, MetaboHUB, CEA Saclay, Gif-sur-Yvette, France.

Bacillus cereus is responsible for foodborne outbreaks worldwide. Among the produced toxins, cereulide induces nausea and vomiting after 30 min to 6 h following the consumption of contaminated foods. Cereulide, a cyclodepsipeptide, is an ionophore selective to K in solution.

View Article and Find Full Text PDF

Cyclosporin A (CycA) is a peptide secondary metabolite derived from fungi that plays a crucial role in transplantation surgery. Cyclic traveling wave ion mobility mass spectrometry (IM-MS) revealed an N → O peptidyl shift in singly protonated CycA to isocyclosporin A (isoA), whereas no such isomerization was observed for doubly protonated and sodiated molecules. CycA and isoA were able to be separated by considering doubly protonated precursors using a specific ion fragment.

View Article and Find Full Text PDF

Application of feature-based molecular networking and MassQL for the MS/MS fragmentation study of depsipeptides.

Front Mol Biosci

August 2023

Nucleus of Bioassays, Biosynthesis, and Ecophysiology of Natural Products (NuBBE), Institute of Chemistry, São Paulo State University (UNESP), Araraquara, Brazil.

The Feature-based Molecular Networking (FBMN) is a well-known approach for mapping and identifying structures and analogues. However, in the absence of prior knowledge about the molecular class, assessing specific fragments and clusters requires time-consuming manual validation. This study demonstrates that combining FBMN and Mass Spec Query Language (MassQL) is an effective strategy for accelerating the decoding mass fragmentation pathways and identifying molecules with comparable fragmentation patterns, such as beauvericin and its analogues.

View Article and Find Full Text PDF

Want AI Summaries of new PubMed Abstracts delivered to your In-box?

Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!