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The impact of leaving group anomericity on the structure of glycosyl cations of protected galactosides

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Moon,  Soo-Yeon
Kerry Gilmore, Biomolekulare Systeme, Max Planck Institute of Colloids and Interfaces, Max Planck Society;

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Pardo-Vargas,  Alonso
Peter H. Seeberger - Automated Systems, Biomolekulare Systeme, Max Planck Institute of Colloids and Interfaces, Max Planck Society;

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Gilmore,  Kerry
Kerry Gilmore, Biomolekulare Systeme, Max Planck Institute of Colloids and Interfaces, Max Planck Society;

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Seeberger,  Peter H.
Peter H. Seeberger - Automated Systems, Biomolekulare Systeme, Max Planck Institute of Colloids and Interfaces, Max Planck Society;

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Citation

Greis, K., Mucha, E., Lettow, M., Thomas, D., Kirschbaum, C., Moon, S.-Y., et al. (2020). The impact of leaving group anomericity on the structure of glycosyl cations of protected galactosides. ChemPhysChem, 21(17), 1905-1907. doi:10.1002/cphc.202000473.


Cite as: http://hdl.handle.net/21.11116/0000-0006-D2EF-0
Abstract
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. Here 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.