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Epimerization definitions

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  • Epimerization
    Conversion of a molecule into its epimer by altering the configuration at a single chiral center, often at C2 in sugars.
  • Monosaccharide
    Simple sugar molecule that can undergo various isomerizations and tautomerizations under basic conditions.
  • Base Catalysis
    Acceleration of a chemical reaction by a base, often leading to complex mixtures in sugar chemistry.
  • C2 Position
    Second carbon in a sugar ring, commonly involved in stereochemical changes during epimerization.
  • Enolate Mechanism
    Pathway involving deprotonation at the alpha carbon next to a carbonyl, forming an enolate intermediate.
  • Enediol Mechanism
    Route where deprotonation forms a double bond with two hydroxyl groups, creating an enediol intermediate.
  • Alpha Carbon
    Carbon atom adjacent to a carbonyl group, notable for its increased acidity and reactivity in base.
  • Anomer
    Isomer differing at the C1 position in sugars, resulting from mutarotation, not to be confused with epimers at C2.
  • Mutarotation
    Equilibration between different anomers at the C1 position, leading to a mixture of alpha and beta forms.
  • Enolate
    Resonance-stabilized intermediate with a negative charge on the alpha carbon, formed during base-catalyzed reactions.
  • Enediol
    Intermediate featuring a double bond flanked by two hydroxyl groups, central to one pathway of epimerization.
  • Stereochemistry
    Spatial arrangement of atoms in molecules, crucial for understanding changes during epimerization.
  • Racemization
    Loss of stereochemical information at a chiral center, resulting in a mixture of configurations.
  • D-Glucopyranose
    Six-membered ring form of glucose, often used as a model for studying epimerization.
  • D-Mannopyranose
    Monosaccharide formed from D-glucopyranose by inversion at the C2 hydroxyl group.