Gulose

d-Gulose[1]
Gulose
Names
IUPAC name
D-Gulose
Systematic IUPAC name
(3R,4R,5R,6R)-6-(Hydroxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetraol
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
DrugBank
UNII
  • 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 checkY
    Key: GZCGUPFRVQAUEE-FSIIMWSLSA-N checkY
  • 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
  • O=C[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO
Properties
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 checkY☒N ?)

Gulose is an aldohexose sugar. It is a monosaccharide that is very rare in nature, but has been found in archaea, bacteria and eukaryotes.[2] 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.[3]

References

  1. ^ Merck Index, 11th Edition, 4490
  2. ^ 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.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  3. ^ 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.
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