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6-Phosphogluconic acid

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6-Phosphogluconic acid
Skeletal formula of 6-phosphogluconic acid
Space-filling model of the 6-phosphogluconic acid anion
Names
IUPAC name 6-O-Phosphono-D-gluconic acid
Systematic IUPAC name (2R,3S,4R,5R)-2,3,4,5-Tetrahydroxy-6-(phosphonooxy)hexanoic acid
Other names 6-Phosphogluconate
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.011.882 Edit this at Wikidata
MeSH 6-phosphogluconate
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C6H13O10P/c7-2(1-16-17(13,14)15)3(8)4(9)5(10)6(11)12/h2-5,7-10H,1H2,(H,11,12)(H2,13,14,15)/t2-,3-,4+,5-/m1/s1Key: BIRSGZKFKXLSJQ-SQOUGZDYSA-N
  • InChI=1/C6H13O10P/c7-2(1-16-17(13,14)15)3(8)4(9)5(10)6(11)12/h2-5,7-10H,1H2,(H,11,12)(H2,13,14,15)/t2-,3-,4+,5-/m1/s1Key: BIRSGZKFKXLSJQ-SQOUGZDYBT
SMILES
  • O=P(O)(O)OC(O)(O)(O)(O)C(=O)O
Properties
Chemical formula C6H13O10P
Molar mass 276.135 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

6-Phosphogluconic acid (with conjugate base 6-phosphogluconate) is a phosphorylated sugar acid which appears in the pentose phosphate pathway and the Entner–Doudoroff pathway.

During the oxidative phase of the pentose phosphate pathway, it is formed from 6-phosphogluconolactone by 6-phosphogluconolactonase, and in turn, it is converted to ribulose 5-phosphate by phosphogluconate dehydrogenase, in an oxidative decarboxylation which also produces NADPH.

In those microorganisms which host the Entner-Doudoroff pathway, 6-phosphogluconic acid may also be acted upon by 6-phosphogluconate dehydratase to produce 2-keto-3-deoxy-6-phosphogluconate.

Pentose phosphate pathway metabolic intermediates
Oxidative
Nonoxidative
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