Gulose

d-Gulose ^[1]

Gulose
Names
IUPAC names D-Gulose d-gulo-Hexose [2]
Systematic IUPAC name (3R,4R,5R,6R)-6-(Hydroxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetraol
Identifiers
CAS Number	4205-23-6 (d) Y 6027-89-0 (l) Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:37695  Y
ChemSpider	146783  Y
DrugBank	DB01914  Y
PubChem CID	167792
UNII	25008KX916  (d) Y J96E9Q45N7  (l) Y
InChI InChI=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 Y Key: GZCGUPFRVQAUEE-FSIIMWSLSA-N Y 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 Key: GZCGUPFRVQAUEE-FSIIMWSLBF
SMILES O=C[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO
Properties
Chemical formula	C6H12O6
Molar mass	180.156 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N  verify  (what is  YN ?) Infobox references

Gulose is an aldohexose sugar. It is a monosaccharide that is very rare in nature, but has been found in archaea, bacteria and eukaryotes. ^[3] It also exists as a syrup with a sweet taste. It is soluble in water and slightly soluble in methanol. Neither the d- nor l-forms are fermentable by yeast.

D-Gulose is a C-3 epimer of D-galactose and a C-5 epimer of L-mannose. ^[4]

References

1. Merck Index , 11th Edition, 4490
2. https://iupac.qmul.ac.uk/2carb/app.html
3. Swain, M., Brisson, J. R., Sprott, G. D., Cooper, F. P. and Patel, G. B. (1997). "Identification of β-L-gulose as the sugar moiety of the main polar lipid Thermoplasma acidophilum". Biochim. Biophys. Acta. 1345 (1): 56–64. doi:10.1016/s0005-2760(96)00163-4. PMID   9084501.
4. Zhang, Qingju; et al. (2016). "On the Reactivity of Gulose and Guluronic Acid Building Blocks in the Context of Alginate Assembly". European Journal of Organic Chemistry. 2016 (14): 2393–2397. doi:10.1002/ejoc.201600336.