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Glycoside definitions

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  • O-Glycosidation
    Selective reaction at the anomeric position of monosaccharides in acid, forming an acetal with an R group attached to oxygen.
  • Monosaccharide
    Simple sugar molecule capable of undergoing selective reactions at its anomeric position under acidic conditions.
  • Anomeric Position
    Carbon in a sugar ring where unique reactivity allows formation of acetals, leading to glycoside creation.
  • O-Glycoside
    Acetal product formed when an R group is attached to the anomeric oxygen of a monosaccharide.
  • Acetal
    Functional group with two OR groups bonded to the same carbon, resulting from glycosidation at the anomeric carbon.
  • Fischer Glycosidation
    Acid-catalyzed process similar to Fischer esterification, converting a sugar's anomeric alcohol into an O-glycoside.
  • Fischer Esterification
    Classic acid-catalyzed reaction forming esters from carboxylic acids and alcohols, analogous to glycosidation.
  • Beta-D-Glucopyranose
    Common cyclic form of glucose used as a starting material in O-glycosidation reactions.
  • Oxocarbenium Cation
    Resonance-stabilized intermediate with a positive charge, crucial for the specificity of glycosidation at the anomeric position.
  • Resonance Structure
    Alternative electron arrangements that stabilize intermediates like the oxocarbenium cation during glycosidation.
  • Alpha Anomer
    Stereoisomer of a glycoside where the OR group at the anomeric carbon is trans to the CH2OH group.
  • Beta Anomer
    Stereoisomer of a glycoside where the OR group at the anomeric carbon is cis to the CH2OH group.
  • Mutarotation
    Equilibration process between alpha and beta anomers, resulting in a mixture of glycoside stereoisomers.
  • Acid Catalyst
    Substance that donates protons to initiate and accelerate the glycosidation reaction at the anomeric position.
  • Leaving Group
    Atom or group that departs with a pair of electrons during the formation of the oxocarbenium cation in glycosidation.