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27244-54-8

27244-54-8 Structure

27244-54-8 Structure
IdentificationBack Directory
[Name]

4,5-dihydroxy-2-oxo-6-phosphonooxy-hexanoic acid
[CAS]

27244-54-8
[Synonyms]

KDPG
2-Keto-3-deoxy-6-phosphogluconate
2-Keto-3-deoxy-6-phosphogluconic acid
2-dehydro-3-deoxy-6-phospho-D-gluconic acid
3-Deoxy-2-keto-6-phospho-D-gluconate lithium
2-Keto-3-deoxy-6-phosphogluconate lithium salt
4,5-dihydroxy-2-oxo-6-phosphonooxy-hexanoic acid
2-Keto-2,3-dideoxy-6-O-phosphono-D-gluconic acid
3-deoxy-D-erythro-hex-2-ulosonic acid 6-phosphate
3-Deoxy-2-keto-6-phospho-D-gluconate lithium salt
3-Deoxy-2-keto-6-phosphogluconic acid lithium salt
2-Dehydro-3-deoxy-6-phospho-D-gluconate lithium salt
3-Deoxy-D-erythro-2-hexulosonic acid 6-phosphoric acid
3-Deoxy-2-keto-D-gluconic acid 6-phosphate lithium salt
3-Deoxy-D-erythro-hexulosonic acid 6-phosphate lithium salt
D-erythro-2-Hexulosonic acid, 3-deoxy-, 6-(dihydrogen phosphate)
(4S,5R)-4,5-Dihydroxy-2-oxo-6-phosphonooxyhexanoic acid lithium salt
[Molecular Formula]

C6H11O9P
[MOL File]

27244-54-8.mol
[Molecular Weight]

258.12
Chemical PropertiesBack Directory
[storage temp. ]

-20°C
[form ]

powder
[color ]

white
[Optical Rotation]

[α]/D 9.0±1.0°, 3 hr, c = 0.1 in H2O
[InChI]

1S/C6H11O9P/c7-3(1-4(8)6(10)11)5(9)2-15-16(12,13)14/h3,5,7,9H,1-2H2,(H,10,11)(H2,12,13,14)/t3-,5+/m0/s1
[InChIKey]

OVPRPPOVAXRCED-WVZVXSGGSA-N
[SMILES]

[P](=O)(OC[C@@H](O)[C@@H](O)CC(=O)C(=O)O)(O)O
Safety DataBack Directory
[WGK Germany ]

3
[Storage Class]

11 - Combustible Solids
Hazard InformationBack Directory
[Definition]

ChEBI: The 5-phospho derivative of 2-dehydro-D-gluconic acid.
[Biological Activity]

2-dehydro-3-deoxy-phosphogluconate is a substrate for the enzyme 2-dehydro-3-deoxy-phosphogluconate aldolase which converts it into D-glyceraldehyde 3-phosphate plus pyruvate. ''Metabolite in the pentose phosphate pathwaygenerating NADPH and pentoses; and in the in pentose and glucuronate interconversions; key intermediate in the Entner-Doudoroff pathway of some bacteriasubstrate of 2-Keto-3-deoxy-6-phosphogluconate (KDPG) aldolasecatalyzing the reversible cleavage of KDPG to pyruvate and glyceraldehyde-3-phosphate. It was found to be the carbon catabolite repression signal of phenylacetic acid metabolism in P. putida KT2440. Expression from Pu was repressed mainly via PtsN in response to high levels of 2-dehydro-3-deoxygluconate-6-phosphate.
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