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Quantifying the electronic effects of carbohydrate hydroxy groups by using aminosugar models.

Christian M Pedersen1, Jacob Olsen, Azra B Brka

  • 1Department of Chemistry, University of Copenhagen, 2100 Copenhagen Ø, Denmark. cmp@chem.ku.dk

Chemistry (Weinheim an Der Bergstrasse, Germany)
|May 5, 2011
PubMed
Summary

Researchers synthesized methyl amino-deoxy-glycosides and measured their acidity (pK(a)). Basicity of amino groups in carbohydrates generally follows the order 6-NH(2)>3-NH(2)>2-NH(2)>4-NH(2), influenced by substituent positions.

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Area of Science:

  • Carbohydrate Chemistry
  • Organic Chemistry
  • Physical Organic Chemistry

Background:

  • Amino-deoxy-glycosides are crucial derivatives of common glycosyl acceptors.
  • Understanding their chemical properties informs carbohydrate modification strategies.

Purpose of the Study:

  • To synthesize methyl amino-deoxy-glycosides with varying stereochemistry and amino group positions.
  • To determine the acidity (pK(a)) of these compounds and evaluate electron density.
  • To establish trends in amino group basicity within carbohydrate structures.

Main Methods:

  • Synthesis of diverse methyl amino-deoxy-glycoside analogs.
  • Potentiometric titration for pK(a) value determination.
  • Analysis of stereochemistry and substituent effects on basicity.

Main Results:

  • Synthesized compounds included α- and β-gluco, α-galacto, and α-manno stereoisomers.
  • Established a basicity order for amino groups: 6-NH(2)>3-NH(2)>2-NH(2)>4-NH(2).
  • Observed increased basicity with axial substituents and decreased basicity when the amine is antiperiplanar to oxygen.

Conclusions:

  • The study provides quantitative data on the basicity of amino-deoxy-glycosides.
  • Findings correlate electron density with substituent effects and stereochemistry.
  • Results support observations in glycosylation and regioselective sugar protection chemistry.