Publication

Stereoselectivity of Galactosylation Reactions In Vacuo

2026

Abstract

Controlling the stereoselective outcome of glycosidic bond formation remains a major challenge in chemical synthesis. This process typically proceeds along a complex SN1-SN2 mechanistic continuum. In solution, the key contributions to these mechanisms are difficult to determine due to influence by structural and environmental variables, such as solvents, counterions or temperature. To isolate the intrinsic factors driving steroselectivity in glycosylations, we investigate the reactions for the monosaccharide galactose in the gas phase. We perform ion–molecule galactosylation reactions in complete isolation inside an ion trap of a mass spectrometer and directly probe the stereochemistry of the formed products using mass-resolved ultraviolet cold ion spectroscopy. The results show that α-selectivity is significantly weaker in the gas phase than in solution, and that the product stereochemistry might be influenced by the nucleophile’s electron density rather than its overall nucleophilic strength.

Official source

https://infoscience.epfl.ch/entities/publication/1bc595f6-9d91-4567-b382-be4a85036a65

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2026

Abstract

Official source

https://infoscience.epfl.ch/entities/publication/1bc595f6-9d91-4567-b382-be4a85036a65

About this result

Related concepts (32)

Ion trap

An ion trap is a combination of electric and/or magnetic fields used to capture charged particles — known as ions — often in a system isolated from an external environment. Atomic and molecular ion traps have a number of applications in physics and chemistry such as precision mass spectrometry, improved atomic frequency standards, and quantum computing. In comparison to neutral atom traps, ion traps have deeper trapping potentials (up to several electronvolts) that do not depend on the internal electronic structure of a trapped ion.

Mass spectrometry

Mass spectrometry (MS) is an analytical technique that is used to measure the mass-to-charge ratio of ions. The results are presented as a mass spectrum, a plot of intensity as a function of the mass-to-charge ratio. Mass spectrometry is used in many different fields and is applied to pure samples as well as complex mixtures. A mass spectrum is a type of plot of the ion signal as a function of the mass-to-charge ratio.

Quadrupole ion trap

In experimental physics, a quadrupole ion trap or paul trap is a type of ion trap that uses dynamic electric fields to trap charged particles. They are also called radio frequency (RF) traps or Paul traps in honor of Wolfgang Paul, who invented the device and shared the Nobel Prize in Physics in 1989 for this work. It is used as a component of a mass spectrometer or a trapped ion quantum computer. A charged particle, such as an atomic or molecular ion, feels a force from an electric field.

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Stereoselectivity of Galactosylation Reactions In Vacuo

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