Pentose
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Overview
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-CH HO-CH | | | | HC-OH HC-OH HC-OH HC-OH | | | | CH2OH CH2OH CH2OH CH2OH D-Ribose D-Arabinose D-Xylose D-Lyxose
A mnemonic suggested that can be used to remember the four D-aldopentoses is "ribs are extra lean."
The ketopentoses have 2 chiral centres and therefore 4 possible stereoisomers — ribulose (L- and D-form) and xylulose (L- and D-form).
The D-isomers of both are known to occur naturally as is the L-isomer of xylulose:
CH2OH CH2OH | | C=O C=O | | HC-OH HO-CH | | HC-OH HC-OH | | CH2OH CH2OH D-Ribulose D-Xylulose
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
Acknowledgement and Attribution Regarding Sources of Content
Some of the initial content on this page may be incorporated in part from copyleft sources in the public domain including wikis such as Wikipedia and AskDrWiki. Drug information for patients came from the The National Library of Medicine. Infectious disease information may have come from the Centers for Disease Control (CDC). Differential Diagnoses are drawn from clinicians as well as an amalgamation of 3 sources: 1.The Disease Database; 2. Kahan, Scott, Smith, Ellen G. In A Page: Signs and Symptoms. Malden, Massachusetts: Blackwell Publishing, 2004:3; 3. Sailer, Christian, Wasner, Susanne. Differential Diagnosis Pocket. Hermosa Beach, CA: Borm Bruckmeir Publishing LLC, 2002:7 .
