Carbohydrate Structure

Formerly the name "carbohydrate" was used in chemistry for any compound with the formula C''m''(H2O)''n''. Following this definition, some chemists considered formaldehyde CH2O to be the simplest carbohydrate, while others claimed that title for glycolaldehyde Today the term is generally understood in the biochemistry sense, which excludes compounds with only one or two carbons.

Natural saccharides are generally built of simple carbohydrates called monosaccharides with general formula (CH2O)''n'' where ''n'' is three or more. A typical monosaccharide has the structure H-(CHOH)''x''(C=O)-(CHOH)''y''-H, that is, an aldehyde or ketone with many hydroxyl groups added, usually one on each carbon atom that is not part of the aldehyde or ketone functional group. Examples of monosaccharides are glucose, fructose, and glyceraldehyde. However, some biological substances commonly called "monosaccharides" do not conform to this formula (e.g., uronic acids and deoxy-sugars such as fucose), and there are many chemicals that do conform to this formula but are not considered to be monosaccharides (e.g., formaldehyde CH2O and inositol (CH2O)6).

The open-chain form of a monosaccharide often coexists with a closed ring form where the oxygen of the carbonyl group C=O is replaced by an internal -O- bridge.

Monosaccharides can be linked together into what are called polysaccharides (or oligosaccharides) in a large variety of ways. Many carbohydrates contain one or more modified monosaccharide units that have had one or more groups replaced or removed. For example, deoxyribose, a component of DNA, is a modified version of ribose; chitin is composed of repeating units of N-acetylglucosamine, a nitrogen-containing form of glucose.

Carbohydrate chemistry is a large and economically important branch of organic chemistry. Some of the main organic reactions that involve carbohydrates are:

  • Carbohydrate acetalisation
  • Cyanohydrin reaction
  • Lobry-de Bruyn-van Ekenstein transformation
  • Amadori rearrangement
  • Nef reaction
  • Wohl degradation
  • Koenigs-Knorr reaction

Further Reading

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