Gulose

{{Short description|Rare monosaccharide not fermentable by yeast}} {{chembox | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 451893817 | Name = {{sm|d}}-Gulose | Reference = <ref>''Merck Index'', 11th Edition, '''4490'''</ref> | ImageFile = Gulose.svg | ImageClass = skin-invert | ImageSize = 180px | ImageName = Gulose | IUPACName = D-Gulose {{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 sugar. It is a monosaccharide that is very rare in nature, but has been found in archaea, bacteria and 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. Neither the {{sm|d}}- nor {{sm|l}}-forms are fermentable by yeast.

D-Gulose is a C-3 epimer of D-galactose and a C-5 epimer of L-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}}

Category:Aldohexoses Category:Pyranoses