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Gulose: Difference between revisions

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| Section2 = {{Chembox Properties | Section2 = {{Chembox Properties
|C=6|H=12|O=6 |C=6|H=12|O=6
|MeltingPt = syrup |MeltingPt =
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'''Gulose''' is an ] sugar. It is a ] that is very rare in nature, but has been found in ], ] and ].<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 ]. Neither the {{sm|d}}- nor {{sm|l}}-forms are fermentable by ]. '''Gulose''' is an ] sugar. It is a ] that is very rare in nature, but has been found in ], ] and ].<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 ]. Neither the {{sm|d}}- nor {{sm|l}}-forms are fermentable by ].


<small>D</small>-Gulose is a C-3 ] of ] and a C-5 epimer of ].<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> <small>D</small>-Gulose is a C-3 ] of ] and a C-5 epimer of ].<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>

Latest revision as of 18:39, 23 March 2024

Rare monosaccharide not fermentable by yeast
d-Gulose
Gulose
Names
IUPAC name D-Gulose
Systematic IUPAC name (3R,4R,5R,6R)-6-(Hydroxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetraol
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
DrugBank
PubChem CID
UNII
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/s1Key: GZCGUPFRVQAUEE-FSIIMWSLSA-N
  • 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/s1Key: GZCGUPFRVQAUEE-FSIIMWSLBF
SMILES
  • O=C(O)(O)(O)(O)CO
Properties
Chemical formula C6H12O6
Molar mass 180.156 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒verify (what is  ?) Infobox references
Chemical compound

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

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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Types of carbohydrates
General
Geometry
Monosaccharides
Dioses
Trioses
Tetroses
Pentoses
Hexoses
Heptoses
Above 7
Multiple
Disaccharides
Trisaccharides
Tetrasaccharides
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oligosaccharides
Polysaccharides
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