Pentose

From Academic Kids

A pentose is a monosaccharide with five carbon atoms.

They either have an aldehyde functional group in position 1 (aldopentoses), or a ketone functional group in position 2 (ketopentoses).

The aldopentoses have three chiral centres ("asymmetric carbon atoms") and so 8 different stereoisomers are possible.

The 4 D-aldopentoses are :-

 CH=O        CH=O          CH=O         CH=O
 |           |             |            |
HC-OH     HO-CH           HC-OH      HO-CH
 |           |             |            |
HC-OH       HC-OH       HO-C         HO-CH
 |           |             |            |
HC-OH       HC-OH         HC-OH        HC-OH
 |           |             |            |
 CH2OH       CH2OH         CH2OH        CH2OH
D-Ribose    D-Arabinose   D-Xylose    D-Lyxose

The ketopentoses have 2 chiral centres and therefore 4 possible stereoisomers - ribulose (L- and D- form) and xylulose (L- and D- form).

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 furan, and is termed a furanose. 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.

Ribose is a constituent of RNA, and the related Deoxyribose of DNA.

See also

es:Pentosa eo:Pentozo fr:Pentose id:Pentosa it:Pentosi pl:Pentoza su:Péntosa

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