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 L-Xylulose
Systematic IUPAC name (3R,4S)-1,3,4,5-Tetrahydroxypentan-2-one
Other names threo-Pentulose threo-2-Pentulose
Identifiers
CAS Number	5962-29-8 (D/L)^Y 551-84-8 (D)^Y 527-50-4 (L)^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:17399^Y
ChemSpider	20892^Y
PubChem CID	22253
UNII	9N4LZL67SA^Y YSC9WAF8X1 (D)^Y DL1M07LQ7A (L)^Y
InChI 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
SMILES C([C@@H]([C@H](C(=O)CO)O)O)O
Properties
Chemical formula	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.