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Epimerization and Enediol rearrangement are the two most common unwanted side reactions which can occur when monosaccharides are treated with base.
Epimerization is a process in stereochemistry in which there is a change in the configuration of only one chiral centre. As a result, a diastereomer is formed. The classical example of this in medicine is tetracycline. In acidic conditions around pH 4, tetracycline readily undergoes epimerization at position 4, and an inactive 4-epitetracycline is produced, which on dehydration forms 4-epianhydrotetracycyline, a highly toxic product. This toxic compound can also be formed from acid catalysed (at lower pH) dehydration of tetracycline via anhydrotetracycline.
Enediol rearrangement is a transformation which occurs at basic medium and allows the conversion of epimers, defined as isomeric forms that differ in the position of the hydroxyl group at C-2. In this way it is possible to transform through the enediol intermediate glucose to mannose and vice versa.
Another important isomerization process through the enediol rearrangement is the interconversion of glucose and fructose. Thus, the enolization proceeds by migration of proton at position 2, to carbon at 1.
Monosaccharides contain both alcohol and carbonyl functional groups. This allows monosaccharides to undergo many of the reactions typical for these functional groups. In particular, alcohols can be converted to esters, converted to ethers, converted to acetals, or oxidized. Carbonyls can be reacted with nucleophiles, be reduced to form alcohols, or be oxidized to form carboxylic acids.
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