# Gulose

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> Markdown URL: https://mediated.wiki/source/Gulose.md
> Source: https://en.wikipedia.org/wiki/Gulose
> Source revision: 1305981357
> License: Creative Commons Attribution-ShareAlike 4.0 International (https://creativecommons.org/licenses/by-sa/4.0/)

{{Short description|Rare monosaccharide not fermentable by yeast}}
{{chembox
| Verifiedfields = changed
| Watchedfields  = changed
| verifiedrevid  = 451893817
| Name           = {{sm|d}}-Gulose
| Reference      = <ref>''[Merck Index](/source/Merck_Index)'', 11th Edition, '''4490'''</ref>
| ImageFile      = Gulose.svg
| ImageClass     = skin-invert 
| ImageSize      = 180px
| ImageName      = Gulose
| IUPACName      = <small>D</small>-Gulose
<br>{{sm|d}}-''gulo''-Hexose<ref>https://iupac.qmul.ac.uk/2carb/app.html</ref>
| SystematicName = (3''R'',4''R'',5''R'',6''R'')-6-(Hydroxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetraol
| Section1       = {{Chembox Identifiers
|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
|ChemSpiderID = 146783
|PubChem = 167792
|InChI = 1/C6H12O6/c7-1-3(9)5(11)6(12)4(10)2-8/h1,3-6,8-12H,2H2/t3-,4+,5-,6-/m0/s1
|InChIKey = GZCGUPFRVQAUEE-FSIIMWSLBF
|StdInChI_Ref = {{stdinchicite|correct|chemspider}}
|StdInChI = 1S/C6H12O6/c7-1-3(9)5(11)6(12)4(10)2-8/h1,3-6,8-12H,2H2/t3-,4+,5-,6-/m0/s1
|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
|StdInChIKey = GZCGUPFRVQAUEE-FSIIMWSLSA-N
|CASNo_Ref = {{cascite|correct|??}}
|CASNo = 4205-23-6
|CASNo_Comment = ({{sm|d}})
|CASNo2_Ref = {{cascite|correct|CAS}}
|CASNo2 = 6027-89-0
|CASNo2_Comment = ({{sm|l}})
|UNII_Ref = {{fdacite|correct|FDA}}
|UNII = 25008KX916
|UNII_Comment = ({{sm|d}})
|UNII2_Ref = {{fdacite|correct|FDA}}
|UNII2 = J96E9Q45N7
|UNII2_Comment = ({{sm|l}})
|DrugBank_Ref = {{drugbankcite|correct|drugbank}}
|DrugBank = DB01914
|ChEBI_Ref = {{ebicite|correct|EBI}}
|ChEBI = 37695
|SMILES = O=C[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO
}}
| Section2       = {{Chembox Properties
|C=6|H=12|O=6
|MeltingPt = 
}}
}}

'''Gulose''' is an [aldohexose](/source/aldohexose) sugar. It is a [monosaccharide](/source/monosaccharide) that is very rare in nature, but has been found in [archaea](/source/archaea), [bacteria](/source/bacteria) and [eukaryotes](/source/eukaryotes).<ref>{{cite journal | author = Swain, M., Brisson, J. R., Sprott, G. D., Cooper, F. P. and Patel, G. B. | title = Identification of β-L-gulose as the sugar moiety of the main polar lipid Thermoplasma acidophilum | journal = Biochim. Biophys. Acta | volume = 1345 | issue = 1 | pages = 56–64 | year = 1997 | pmid = 9084501 | doi=10.1016/s0005-2760(96)00163-4}}</ref> It also exists as a syrup with a sweet taste. It is soluble in water and slightly soluble in [methanol](/source/methanol). Neither the {{sm|d}}- nor {{sm|l}}-forms are fermentable by [yeast](/source/yeast).

<small>D</small>-Gulose is a C-3 [epimer](/source/epimer) of [<small>D</small>-galactose](/source/galactose) and a C-5 epimer of [<small>L</small>-mannose](/source/mannose).<ref>{{cite journal | author = Zhang, Qingju |display-authors=etal |title=On the Reactivity of Gulose and Guluronic Acid Building Blocks in the Context of Alginate Assembly |journal=European Journal of Organic Chemistry |year=2016 |volume=2016 |issue=14 |pages=2393–2397 |doi=10.1002/ejoc.201600336}}</ref>

==References==
{{reflist}}

{{Carbohydrates}}

Category:Aldohexoses
Category:Pyranoses

{{Ether-stub}}

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Adapted from the Wikipedia article [Gulose](https://en.wikipedia.org/wiki/Gulose) by Wikipedia contributors ([contributor history](https://en.wikipedia.org/wiki/Gulose?action=history)). Available under [Creative Commons Attribution-ShareAlike 4.0 International](https://creativecommons.org/licenses/by-sa/4.0/). Changes may have been made.