AskDefine | Define hexose

Dictionary Definition

hexose n : a monosaccharide that contains six carbon atoms per molecule

User Contributed Dictionary

English

Etymology

From hex and -ose.

Noun

  1. A sugar or saccharide containing six carbon atoms.
    Glucose is a common hexose

Translations

a sugar containing six carbon atoms
  • Spanish: hexosa

Extensive Definition

In organic chemistry, a hexose is a monosaccharide with six carbon atoms having the chemical formula C6H12O6. Hexoses are classified by functional group, with aldohexoses having an aldehyde at position 1, and ketohexoses having a ketone at position 2.

Aldohexoses

The aldohexoses have four chiral centres for a total of 16 possible aldohexose stereoisomers (24). The D/L configuration is based on the orientation of the hydroxyl at position 5, and does not refer to the direction of optical activity. The eight D-aldohexoses are:
CH=O CH=O CH=O CH=O | | | | HC-OH HO-CH HC-OH HO-CH | | | | HC-OH HC-OH HO-CH HO-CH | | | | HC-OH HC-OH HC-OH HC-OH | | | | HC-OH HC-OH HC-OH HC-OH | | | | CH2OH CH2OH CH2OH CH2OH D-Allose D-Altrose D-Glucose D-Mannose
CH=O CH=O CH=O CH=O | | | | HC-OH HO-CH HC-OH HO-CH | | | | HC-OH HC-OH HO-CH HO-CH | | | | HO-CH HO-CH HO-CH HO-CH | | | | HC-OH HC-OH HC-OH HC-OH | | | | CH2OH CH2OH CH2OH CH2OH D-Gulose D-Idose D-Galactose D-Talose
Of these D isomers all, except altrose, are naturally occurring. L-altrose has been isolated from strains of the bacterium Butyrivibrio fibrisolvens.
A mnemonic (attributed to Louis Fieser) often employed to remember the eight aldohexoses is "all altruists gladly make gum in gallon tanks".

Cyclic Hemiacetals

It has been known since 1926 that 6-carbon aldose sugars form cyclic hemiacetals. The diagram below shows the hemiacetal forms for D-glucose and D-mannose.
The numbered carbons in the open chain forms correspond to the same numbered carbons in the hemiacetal forms. The formation of the hemiacetal causes carbon number 1, which is symmetric in the open chain form, to become asymmetric in the cyclic version. This means that both glucose and mannose (as well as all the other aldohexoses) each have two cyclic forms. In solution both of these exist in equilibrium with the open-chain form. The open-chain form, however, does not crystallize. Hence the two cyclic forms become separable when they are crystallized. For example, D-glucose forms an alpha crystal that has specific rotation of +112° and melting point of 146 °C, as well as a beta crystal that has specific rotation of +19° and melting point of 150 °C.

Ketohexoses

Only the naturally occurring hexoses are capable of being fermented by yeasts.

Mutarotation

The aldehyde and ketone functional groups in these carbohydrates react with neighbouring hydroxyl functional groups to form intramolecular hemiacetals or hemiketals, respectively. The resulting ring structure is related to pyran, and is termed a pyranose. The ring spontaneously opens and closes, allowing rotation to occur about the bond between the carbonyl group and the neighbouring carbon atom, yielding two distinct configurations (α and β). This process is termed mutarotation. Hexose sugars can form dihexose sugars with a condensation reaction to form a 1,6-glycosidic bond.

Other Information

It is a weak acid and a weak electrolyte.

References

See also

hexose in Arabic: هكسوز
hexose in Belarusian (Tarashkevitsa): Гексозы
hexose in Catalan: Hexosa
hexose in Czech: Hexózy
hexose in Danish: Hexose
hexose in German: Hexosen
hexose in Spanish: Hexosa
hexose in Esperanto: Heksozo
hexose in Basque: Hexosa
hexose in French: Hexose
hexose in Italian: Esoso
hexose in Dutch: Hexose
hexose in Japanese: ヘキソース
hexose in Polish: Heksozy
hexose in Russian: Гексозы
hexose in Swedish: Hexos
hexose in Ukrainian: Гексози
hexose in Chinese: 己糖
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