Xylulose: Difference between revisions
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| Reference = <ref>Data is for L-xylulose.</ref><ref>''Merck Index'', 11th Edition, '''9996'''.</ref> |
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| verifiedrevid = 470634402 |
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| ImageFileL1 = L-xylulose.png |
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| Reference = <ref>Data is for L-xylulose.</ref><ref>''Merck Index'', 11th Edition, '''9996'''.</ref> |
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| ImageSizeL1 = |
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| ImageFile1 = Xylulose.png |
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| ImageFileL2 = Alpha-D-Xylulofuranose.svg |
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| ImageSizeR1 = 150px |
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| ImageFileR2 = Beta-D-Xylulofuranose.svg |
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| IUPACName = (''3R,4S'')-1,3,4,5-Tetrahydroxypentan-2-one |
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| SystematicName = (''3R,4S'')-1,3,4,5-Tetrahydroxypentan-2-one |
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| OtherNames = threo-Pentulose<br>threo-2-Pentulose |
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| IUPACName = <small>L</small>-''threo''-Pent-2-ulose |
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| Section1 = {{Chembox Identifiers |
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| OtherNames = threo-Pentulose<br />threo-2-Pentulose<small>L</small>-Xylulose |
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| CASNo = 527-50-4 |
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| Section1 = {{Chembox Identifiers |
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| PubChem = 22253 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| SMILES = C([C@@H]([C@H](C(=O)CO)O)O)O |
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| ChemSpiderID = 20892 |
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}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| Section2 = {{Chembox Properties |
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| StdInChI = 1S/C5H10O5/c6-1-3(8)5(10)4(9)2-7/h3,5-8,10H,1-2H2/t3-,5+/m0/s1 |
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| Formula = C<sub>5</sub>H<sub>10</sub>O<sub>5</sub> |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| MolarMass = 150.13 g/mol |
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| StdInChIKey = ZAQJHHRNXZUBTE-WVZVXSGGSA-N |
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| Appearance = Syrup |
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| InChI = 1S/C5H10O5/c6-1-3(8)5(10)4(9)2-7/h3,5-8,10H,1-2H2/t3-,5+/m0/s1 |
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| Density = |
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| InChIKey1 = ZAQJHHRNXZUBTE-WVZVXSGGSA-N |
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| MeltingPt = |
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| CASNo = 5962-29-8 |
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| BoilingPt = |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| Solubility = |
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| CASNo_Comment = (<small>D</small>/<small>L</small>) |
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}} |
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| CASNo1 = 551-84-8 |
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| Section3 = {{Chembox Hazards |
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| CASNo1_Ref = {{cascite|correct|CAS}} |
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| MainHazards = |
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| CASNo1_Comment = (<small>D</small>) |
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| FlashPt = |
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| CASNo2 = 527-50-4 |
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| Autoignition = |
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| CASNo2_Ref = {{cascite|correct|CAS}} |
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}} |
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| CASNo2_Comment = (<small>L</small>) |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = 9N4LZL67SA |
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| UNII1_Ref = {{fdacite|correct|FDA}} |
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| UNII1 = YSC9WAF8X1 |
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| UNII1_Comment = (<small>D</small>) |
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| UNII2_Ref = {{fdacite|correct|FDA}} |
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| UNII2 = DL1M07LQ7A |
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| UNII2_Comment = (<small>L</small>) |
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| PubChem = 22253 |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI = 17399 |
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| SMILES = C([C@@H]([C@H](C(=O)CO)O)O)O |
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}} |
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| Section2 = {{Chembox Properties |
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| C=5 | H=10 | O=5 |
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| Appearance = colorless syrup |
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| Density = |
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| MeltingPt = |
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| BoilingPt = |
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| Solubility = |
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}} |
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| Section3 = {{Chembox Hazards |
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| MainHazards = |
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| FlashPt = |
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| AutoignitionPt = |
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}} |
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}} |
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'''Xylulose''' is a [[ketopentose]], a [[monosaccharide]] containing five [[carbon]] [[atom]]s, and including a [[ketone]] [[functional group]]. |
'''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> |
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== Pathology == |
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<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]]. |
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== References == |
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In animals, <small>L</small>-Xylulose accumulates in the [[urine]] in patients with [[pentosuria]]. 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]]. |
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== See also == |
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* [[Arabinose]] |
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* [[Deoxyribose]] |
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* [[Lyxose]] |
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* [[Ribose]] |
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* [[Ribulose]] |
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* [[Xylose]] |
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* [[L-xylulose reductase]] |
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==References== |
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{{Reflist}} |
{{Reflist}} |
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==External links== |
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{{ChemicalSources}} |
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[[Category:Ketoses]] |
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[[Category:Monosaccharides]] |
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{{organic-compound-stub}} |
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{{Carbohydrates}} |
{{Carbohydrates}} |
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[[Category:Ketopentoses]] |
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[[de:Xylulose]] |
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[[ |
[[Category:Furanoses]] |
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[[ja:キシルロース]] |
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[[fi:Ksyluloosi]] |
Latest revision as of 02:05, 18 May 2024
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Names | |||
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IUPAC name
L-threo-Pent-2-ulose
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Systematic IUPAC name
(3R,4S)-1,3,4,5-Tetrahydroxypentan-2-one | |||
Other names
threo-Pentulose
threo-2-PentuloseL-Xylulose | |||
Identifiers | |||
3D model (JSmol)
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ChEBI | |||
ChemSpider | |||
PubChem CID
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UNII |
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CompTox Dashboard (EPA)
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Properties | |||
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).
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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.