Sulfoquinovose

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Sulfoquinovose
Sulfoquinovose chemical structure.png
Names
IUPAC name
6-Deoxy-6-sulfo-D-glucopyranose
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
PubChem CID
UNII
  • InChI=1S/C6H12O8S/c7-3-2(1-15(11,12)13)14-6(10)5(9)4(3)8/h2-10H,1H2,(H,11,12,13)/t2-,3-,4+,5-,6?/m1/s1
  • O=S(=O)(O)C[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O
Properties
C6H12O8S
Molar mass 244.21 g·mol−1
Melting point 132–138 °C (270–280 °F; 405–411 K)(dec.) [1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Sulfoquinovose, also known as 6-sulfoquinovose and 6-deoxy-6-sulfo-D-glucopyranose, is a monosaccharide sugar that is found as a building block in the sulfolipid sulfoquinovosyl diacylglycerol (SQDG). [2] Sulfoquinovose is a sulfonic acid derivative of glucose, the sulfonic acid group is introduced into the sugar by the enzyme UDP-sulfoquinovose synthase (SQD1). Sulfoquinovose is degraded through a metabolic process termed sulfoglycolysis. The half-life for mutarotation of sulfoquinovose at pD 7.5 and 26C is 299 minutes. [3]

See also

Related Research Articles

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Phosphorylation Chemical process of introducing a phosphate

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Sulfoglycolysis is a catabolic process in primary metabolism in which sulfoquinovose (6-deoxy-6-sulfonato-glucose) is metabolized to produce energy and carbon-building blocks. Sulfoglycolysis pathways occur in a wide variety of organisms, and enable key steps in the degradation of sulfoquinovosyl diacylglycerol (SQDG), a sulfolipid found in plants and cyanobacteria into sulfite and sulfate. Sulfoglycolysis converts sulfoquinovose (C6H12O8S) into various smaller metabolizable carbon fragments such as pyruvate and dihydroxyacetone phosphate that enter central metabolism. The free energy is used to form the high-energy molecules ATP (adenosine triphosphate) and NADH (reduced nicotinamide adenine dinucleotide). Unlike glycolysis, which allows metabolism of all carbons in glucose, some sulfoglycolysis pathways convert only a fraction of the carbon content of sulfoquinovose into smaller metabolizable fragments; the remaineder is excreted as C3-sulfonates 2,3-dihydroxypropanesulfonate (DHPS) or sulfolactate (SL); or the C2-sulfonate isethionate.

References

  1. "Life Science Technologies : Sulfoquinovose 250mg".
  2. Goddard-Borger, ED; Williams, SJ (20 February 2017). "Sulfoquinovose in the biosphere: occurrence, metabolism and functions". The Biochemical Journal. 474 (5): 827–849. doi:10.1042/BCJ20160508. PMID   28219973.
  3. Abayakoon, Palika; Lingford, James P.; Jin, Yi; Bengt, Christopher; Davies, Gideon J.; Yao, Shenggen; Goddard-Borger, Ethan D.; Williams, Spencer J. (2018-04-16). "Discovery and characterization of a sulfoquinovose mutarotase using kinetic analysis at equilibrium by exchange spectroscopy". The Biochemical Journal. 475 (7): 1371–1383. doi:10.1042/BCJ20170947. ISSN   1470-8728. PMC   5902678 . PMID   29535276.