The Impact of Leaving Group Anomericity on the Structure of Glycosyl Cations of Protected Galactosides

Journal article

It has been reported that fragments produced by glycosidic bond breakage in mass spectrometry‐based experiments can retain a memory of their anomeric configuration, which has major implications for glycan sequencing. Herein, we use cryogenic vibrational spectroscopy and ion mobility‐mass spectrometry to study the structure of B‐type fragments of protected galactosides. Cationic fragments were generated from glycosyl donors carrying trichloroacetimidate or thioethyl leaving groups of different anomeric configuration. The obtained infrared signatures indicate that the investigated fragments exhibit an identical structure, which suggests that there is no anomeric memory in B‐type ions of fully protected monosaccharides

Authors: Greis, K; Mucha, E; Lettow, M; Thomas, DA; Kirschbaum, C

• Publication status: Published
• Peer review status: Peer reviewed
• Publisher: Wiley
• Journal: ChemPhysChem
• Volume: 21
• Issue: 17
• Pages: 1905-1907
• Publication date: 2020-07-11
• DOI: 10.1002/cphc.202000473
• EISSN: 1439-7641
• ISSN: 1439-4235
• Language: English
• Keywords: Leaving group; Chromatography; Mass spectrometry; Chemistry; Glycoprotein; Monosaccharide; Glycosyl; Glycosidic bond; Glycoside; Organic chemistry; Biochemistry; Cationic polymerization; Crystallography; Galactosides; Glycan; Anomer; Stereochemistry