Xylulose

Xylulose is a ketopentose, a monosaccharide containing five carbon atoms, and including a ketone functional group. It has the chemical formula C5H10O5. In nature, it occurs in both the L- and D-enantiomers.[3] 1-Deoxyxylulose is a precursor to terpenes via the DOXP pathway.[4]

Xylulose[1][2]
Names
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
  • InChI=1S/C5H10O5/c6-1-3(8)5(10)4(9)2-7/h3,5-8,10H,1-2H2/t3-,5+/m0/s1 Y
    Key: ZAQJHHRNXZUBTE-WVZVXSGGSA-N Y
  • InChI=1S/C5H10O5/c6-1-3(8)5(10)4(9)2-7/h3,5-8,10H,1-2H2/t3-,5+/m0/s1
  • Key: ZAQJHHRNXZUBTE-WVZVXSGGSA-N
  • C([C@@H]([C@H](C(=O)CO)O)O)O
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).
N verify (what is YN ?)
Infobox references

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.
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