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Monosaccharides - Ruff Degradation definitions

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  • Ruff Degradation
    A chain-shortening process for sugars that removes one carbon atom per cycle via decarboxylation, yielding a more stereo specific product.
  • Decarboxylation
    A reaction where a carboxylic acid group is removed from a molecule, releasing CO2 and shortening the carbon chain.
  • Kiliani Fischer Reaction
    A chain-lengthening method for sugars that adds a carbon atom, often resulting in two epimers due to a new chiral center.
  • Bromine Water
    A mild oxidizing agent used to convert an aldehyde group in a sugar to a carboxylic acid during the initial step.
  • Carboxylic Acid
    A functional group formed by oxidizing an aldehyde, which can undergo decarboxylation to release CO2.
  • Aldehyde
    A terminal functional group in sugars that is oxidized to a carboxylic acid before chain shortening.
  • Hydrogen Peroxide
    A radical initiator used with iron sulfate to promote decarboxylation and oxidation in the chain-shortening process.
  • Iron Sulfate Complex
    A reagent that, with hydrogen peroxide, facilitates radical decarboxylation and oxidation in Ruff degradation.
  • Radical Mechanism
    A reaction pathway involving unpaired electrons, essential for the decarboxylation and oxidation steps in this process.
  • C2 Stereocenter
    The chiral center at the second carbon of a sugar, which is lost during each cycle, reducing the number of chiral centers.
  • Aldonic Acid
    A carboxylic acid derivative of a sugar formed by oxidizing the aldehyde group, serving as an intermediate in chain shortening.
  • CO2
    A gaseous byproduct released during decarboxylation, representing the loss of one carbon atom from the sugar chain.
  • Epimer
    A stereoisomer differing at only one chiral center, commonly formed in chain-lengthening but not in chain-shortening reactions.
  • Hydroxyl Group
    A functional group remaining unchanged at the terminal positions of the shortened sugar after the reaction.
  • D-Arabinose
    A monosaccharide product formed from D-mannose after chain shortening, retaining the last three hydroxyl groups.