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Direct Experimental Characterization of a Sialyl Cation.

Franziska Dahlmann1,2,3, Caleb E Griesbach4,5, América Y Torres-Boy6

  • 1Department of Chemistry, Yale University, New Haven, 06520, Connecticut, USA.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|November 5, 2024
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Summary

Researchers characterized the sialyl cation intermediate for the first time, revealing a bridged structure that explains the stereoselectivity of sialylation reactions.

Keywords:
carbohydratesglycosylationinfrared spectroscopymass spectrometrysialic acid

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Area of Science:

  • Carbohydrate Chemistry
  • Organic Reaction Mechanisms
  • Spectroscopy

Background:

  • Sialic acids are crucial monosaccharides in biological processes.
  • Controlling stereoselectivity in sialylation reactions remains a significant challenge.
  • Mechanistic studies on the sialyl cation intermediate are limited.

Purpose of the Study:

  • To generate and structurally characterize the elusive sialyl cation.
  • To elucidate the factors governing stereoselectivity in sialylation reactions.
  • To provide mechanistic insights into sialyl cation formation and reactivity.

Main Methods:

  • Generation and isolation of a sialyl cation from an ionized sialic acid precursor.
  • Structural characterization using cryogenic infrared spectroscopy.
  • Computational analysis with quantum chemical calculations.

Main Results:

  • The sialyl cation was successfully generated and isolated.
  • A novel bridged structure of the sialyl cation was identified for the first time.
  • The C5-NHAc group stabilizes the positive charge via remote participation, forming the bridged structure.
  • The bridged structure shields the β-side, explaining observed α-selectivity in SN1 sialylation.

Conclusions:

  • The study provides the first structural characterization of a sialyl cation.
  • The findings explain the α-selectivity in sialylation reactions through a bridged intermediate.
  • This work offers critical mechanistic insights into carbohydrate chemistry and sialylation processes.