Evidence of Gas-phase Pyranose-to-furanose Isomerization in Protonated Peptidoglycans
| Autor: | Benjamin J. Bythell, Shanshan Guan |
|---|---|
| Rok vydání: | 2021 |
| Předmět: |
chemistry.chemical_classification
Stereochemistry General Physics and Astronomy Deuterium Exchange Measurement Glycosidic bond Protonation Peptidoglycan Furanose Tandem mass spectrometry Mass spectrometry Dissociation (chemistry) Isomerism Pyranose chemistry Tandem Mass Spectrometry Isotope Labeling Gases Glycosides Physical and Theoretical Chemistry Isomerization |
| DOI: | 10.33774/chemrxiv-2021-4krdx |
| Popis: | Peptidoglycans are diverse co- and post-translational modifications of key importance in myriad biological processes. Mass spectrometry is employed to infer their biomolecular sequences and stereochemisties, but little is known about the critical gas-phase dissociation processes involved. Here, using tandem mass spectrometry (MS/MS and MSn), isotopic labelling and high-level simulations, we identify and characterize a facile isomerization reaction that produces furanose N-acetylated ions. This reaction occurs for both O- and N-linked peptidoglycans irrespective of glycosidic linkage stereochemistry (α/β). Dissociation of the glycosidic and other bonds thus occur from the furanose isomer critically altering the reaction feasibility and product ion structures. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|