Chemistry:Xylulose

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Xylulose[1][2]
Xylulose.png
Alpha-D-Xylulofuranose.svg
Beta-D-Xylulofuranose.svg
Names
IUPAC name
L-Xylulose
Systematic IUPAC name
(3R,4S)-1,3,4,5-Tetrahydroxypentan-2-one
Other names
threo-Pentulose
threo-2-Pentulose
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
UNII
Properties
C5H10O5
Molar mass 150.13 g/mol
Appearance colorless syrup
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Xylulose is a ketopentose, a monosaccharide containing five carbon atoms, and including a ketone functional group. It has the chemical formula C
5
H
10
O
5
. In nature, it occurs in both the L- and D-enantiomers.[3] 1-Deoxyxylulose is a precursor to terpenes via the DOXP pathway.[4]

Pathology

L-Xylulose accumulates in the urine in patients with pentosuria, due to a deficiency in L-xylulose reductase. Since L-xylulose is a reducing sugar like D-glucose, pentosuria patients have been wrongly diagnosed in the past to be diabetic.

References

  1. Data is for L-xylulose.
  2. Merck Index, 11th Edition, 9996.
  3. Winkelhausen, Eleonora; Kuzmanova, Slobodanka (1998). "Microbial conversion of d-xylose to xylitol". Journal of Fermentation and Bioengineering 86: 1–14. doi:10.1016/S0922-338X(98)80026-3. 
  4. Rohdich, F.; Bacher, A.; Eisenreich, W. (2005). "Isoprenoid biosynthetic pathways as anti-infective drug targets". Biochemical Society Transactions 33 (4): 785–791. doi:10.1042/BST0330785. PMID 16042599.