:Gulose

{{Short description|Rare monosaccharide not fermentable by yeast}}

{{chembox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 451893817

| Name = {{sm|d}}-Gulose

| Reference = Merck Index, 11th Edition, 4490

| ImageFile = Gulose.svg

| ImageSize = 180px

| ImageName = Gulose

| IUPACName = D-Gulose

{{sm|d}}-gulo-Hexosehttps://iupac.qmul.ac.uk/2carb/app.html

| SystematicName = (3R,4R,5R,6R)-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.{{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}} 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.{{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}}