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Labeling monosaccharides with stable isotopes.

Wenhui Zhang1, Shikai Zhao2, Anthony S Serianni1

  • 1Department of Chemistry and Biochemistry, University of Notre Dame, Notre Dame, Indiana, USA.

Methods in Enzymology
|November 19, 2015
PubMed
Summary
This summary is machine-generated.

This study details chemical and chemi-enzymic methods for creating isotopically labeled monosaccharides using stable isotopes like carbon-13 and nitrogen-15. Key reactions include cyanohydrin reduction and molybdate-catalyzed epimerization for versatile biomolecule synthesis.

Keywords:
(13)C-labeled sugarsChemi-enzymic synthesis of labeled saccharidesCyanohydrin reductionDeuterium-labeled sugarsIsotopically labeled 2-ketosesIsotopically labeled aldosesMolybdate-catalyzed epimerization of aldosesMultiply labeled monosaccharidesOxygen-labeled sugarsSingly labeled monosaccharides

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Area of Science:

  • Carbohydrate Chemistry
  • Isotope Chemistry
  • Biochemistry

Background:

  • Monosaccharide isotopomers are crucial for metabolic studies and understanding complex biomolecules.
  • Existing methods for isotopic labeling often have limitations in scope or efficiency.

Purpose of the Study:

  • To review and detail chemical and chemi-enzymic methods for preparing singly and multiply labeled monosaccharide isotopomers.
  • To focus on the incorporation of stable isotopes (13C, 2H, 17/18O, 15N) into monosaccharides.

Main Methods:

  • Discussion of chemical methods for stable isotope incorporation.
  • Detailed examination of cyanohydrin reduction (CR) and molybdate-catalyzed epimerization (MCE).
  • Exploration of integrating chemical synthesis with enzyme-mediated processes.

Main Results:

  • CR and MCE are presented as primary reactions for isotope insertion.
  • Mechanistic features, advantages, and limitations of CR and MCE are analyzed.
  • A framework for preparing diverse labeled monosaccharides is outlined.

Conclusions:

  • Chemical and chemi-enzymic strategies provide versatile routes to isotopically labeled monosaccharides.
  • These labeled monosaccharides are essential building blocks for complex isotopically labeled biomolecules.
  • The described methods facilitate advancements in metabolic tracing and structural biology.