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Monosaccharides - Aldose-Ketose Rearrangement definitions

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  • Monosaccharide
    Simple carbohydrate unit that can undergo multiple structural changes in basic conditions, leading to various isomers.
  • Aldose
    Sugar containing an aldehyde group, capable of rearranging into a ketose under basic conditions via enediol intermediates.
  • Ketose
    Sugar containing a ketone group, often formed from aldoses through base-catalyzed rearrangement involving enediol intermediates.
  • Enediol
    Intermediate with adjacent hydroxyl groups on a double-bonded carbon chain, crucial for both epimerization and rearrangement reactions.
  • Epimerization
    Process where the configuration at a single stereocenter, often C2, is inverted, producing a different stereoisomer.
  • Aldose-Ketose Rearrangement
    Transformation where an aldose is converted into a ketose, or vice versa, through an enediol intermediate in basic solution.
  • Lobry de Bruyn Van Ekenstein Reaction
    Historical name for the base-catalyzed interconversion between aldoses and ketoses via enediol intermediates.
  • Alpha Hydrogen
    Hydrogen atom attached to the carbon adjacent to the carbonyl group, whose removal initiates enediol formation.
  • Isomerization
    Conversion of a molecule into another molecule with the same atoms but a different arrangement, often leading to new sugars.
  • Anomer
    Type of stereoisomer differing at the hemiacetal or hemiketal carbon, such as alpha and beta forms of glucose.
  • Mannose
    C-2 epimer of glucose, formed through base-catalyzed epimerization involving an enediol intermediate.
  • Fructose
    Ketohexose produced from glucose via aldose-ketose rearrangement, involving carbonyl migration to C2.
  • Enolate
    Resonance-stabilized anion formed after deprotonation of an alpha hydrogen, serving as a key intermediate in rearrangements.
  • Basic Conditions
    Environment with excess hydroxide ions, promoting tautomerization, isomerization, and rearrangement of sugars.
  • Tautomerization
    Rapid interconversion between structural isomers, such as between aldehyde and enediol forms, under basic conditions.