Xylulose: Difference between revisions

Xylulose^[1]^[2]
Names
	IUPAC name L-threo-Pent-2-ulose
	Systematic IUPAC name (3R,4S)-1,3,4,5-Tetrahydroxypentan-2-one
	Other names threo-Pentulose; threo-2-PentuloseL-Xylulose
Identifiers
CAS Number	5962-29-8 (D/L) ; 551-84-8 (D) ; 527-50-4 (L) ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:17399 ;
ChemSpider	20892 ;
PubChem CID	22253;
UNII	9N4LZL67SA ; YSC9WAF8X1 (D) ; DL1M07LQ7A (L) ;
CompTox Dashboard (EPA)	DTXSID201315618 ;
	InChI 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 ; 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	150.130 g·mol−1
Appearance	colorless syrup
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

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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]

Pathology[edit]

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[edit]

^ Data is for L-xylulose.
^ Merck Index, 11th Edition, 9996.
^ 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.
^ 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.

[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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[3]

[4]

@@ Line 1: / Line 1: @@
 {{chembox
 | Verifiedfields = changed
-| verifiedrevid = 470634402
+| verifiedrevid  = 470634402
-| Reference = <ref>Data is for L-xylulose.</ref><ref>''Merck Index'', 11th Edition, '''9996'''.</ref>
+| Reference      = <ref>Data is for L-xylulose.</ref><ref>''Merck Index'', 11th Edition, '''9996'''.</ref>
-| ImageFile1 = Xylulose.png
+| ImageFile1     = Xylulose.png
-| ImageFileL2 =Alpha-D-Xylulofuranose.svg
+| ImageFileL2    = Alpha-D-Xylulofuranose.svg
-| ImageFileR2 =Beta-D-Xylulofuranose.svg
+| ImageFileR2    = Beta-D-Xylulofuranose.svg
-| IUPACName = (''3R,4S'')-1,3,4,5-Tetrahydroxypentan-2-one
+| SystematicName = (''3R,4S'')-1,3,4,5-Tetrahydroxypentan-2-one
-| OtherNames = threo-Pentulose<br />threo-2-Pentulose
+| IUPACName      = <small>L</small>-''threo''-Pent-2-ulose
+| OtherNames     = threo-Pentulose<br />threo-2-Pentulose<small>L</small>-Xylulose
-| Section1 = {{Chembox Identifiers
+| Section1       = {{Chembox Identifiers
 | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
 | ChemSpiderID = 20892
@@ Line 38: / Line 39: @@
 | ChEBI = 17399
 | SMILES = C([C@@H]([C@H](C(=O)CO)O)O)O
-  }}
+ }}
-| Section2 = {{Chembox Properties
+| Section2       = {{Chembox Properties
+| C=5 | H=10 | O=5
-| Formula = C<sub>5</sub>H<sub>10</sub>O<sub>5</sub>
-| MolarMass = 150.13 g/mol
 | Appearance = colorless syrup
 | Density =
@@ Line 47: / Line 47: @@
 | BoilingPt =
 | Solubility =
-  }}
+ }}
-| Section3 = {{Chembox Hazards
+| Section3       = {{Chembox Hazards
 | MainHazards =
 | FlashPt =
 | AutoignitionPt =
-  }}
+ }}
 }}
-'''Xylulose''' is a [[ketopentose]], a [[monosaccharide]] containing five [[carbon]] [[atom]]s, and including a [[ketone]] [[functional group]].  It has the [[chemical formula]] {{carbon}}<sub>5</sub>{{hydrogen}}<sub>10</sub>{{oxygen}}<sub>5</sub>.  In nature, it occurs in both the <small>L</small>- and <small>D</small>-[[enantiomer]]s.<ref>{{cite journal |doi=10.1016/S0922-338X(98)80026-3|title=Microbial conversion of d-xylose to xylitol|year=1998|last1=Winkelhausen|first1=Eleonora|last2=Kuzmanova|first2=Slobodanka|journal=Journal of Fermentation and Bioengineering|volume=86|pages=1–14}}</ref> 1-Deoxyxylulose is a precursor to [[terpene]]s via the non[[mevalonic acid pathway]].<ref>{{cite journal |doi=10.1042/BST0330785|title=Isoprenoid biosynthetic pathways as anti-infective drug targets|year=2005|last1=Rohdich|first1=F.|last2=Bacher|first2=A.|last3=Eisenreich|first3=W.|journal=Biochemical Society Transactions|volume=33|issue=4|pages=785–791|pmid=16042599}}</ref>
+'''Xylulose''' is a [[ketopentose]], a [[monosaccharide]] containing five [[carbon]] [[atom]]s, and including a [[ketone]] [[functional group]]. It has the [[chemical formula]] {{chem2|auto=1|C5H10O5}}. In nature, it occurs in both the <small>L</small>- and <small>D</small>-[[enantiomer]]s.<ref>{{cite journal |doi=10.1016/S0922-338X(98)80026-3|title=Microbial conversion of d-xylose to xylitol|year=1998|last1=Winkelhausen|first1=Eleonora|last2=Kuzmanova|first2=Slobodanka|journal=Journal of Fermentation and Bioengineering|volume=86|pages=1–14}}</ref> 1-Deoxyxylulose is a precursor to [[terpene]]s via the [[DOXP pathway]].<ref>{{cite journal |doi=10.1042/BST0330785|title=Isoprenoid biosynthetic pathways as anti-infective drug targets|year=2005|last1=Rohdich|first1=F.|last2=Bacher|first2=A.|last3=Eisenreich|first3=W.|journal=Biochemical Society Transactions|volume=33|issue=4|pages=785–791|pmid=16042599}}</ref>
 == Pathology ==
 <small>L</small>-Xylulose accumulates in the [[urine]] in patients with [[pentosuria]], due to a deficiency in [[L-xylulose reductase]]. Since <small>L</small>-xylulose is a reducing sugar like [[D-glucose|<small>D</small>-glucose]], pentosuria patients have been wrongly diagnosed in the past to be [[diabetic]].
@@ Line 65: / Line 65: @@
 [[Category:Ketopentoses]]
+[[Category:Furanoses]]