2-Keto-3-deoxy-D-gluconic acid (ECMDB01353) (M2MDB000352)
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Version | 2.0 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Creation Date | 2012-05-31 13:50:40 -0600 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Update Date | 2015-09-17 19:21:29 -0600 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Secondary Accession Numbers |
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Identification | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Name: | 2-Keto-3-deoxy-D-gluconic acid | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Description | 2-keto-3-deoxy-D-gluconic acid is a member of the chemical class known as Hexoses. These are monosaccharides in which the sugar unit is a hexose. KDG, an actual inducer of pectinolysis, releases the repressor from the operator complexes, whereas galacturonate, which is the precursor of the actual inducer, does not. (PMID 1545709) KDG aldolase, KDGA, is a homotetramer of 32-kDa subunits. (PMID 20023024) The KDG-aldolase is a thermostable tetrameric protein with a half-life at 100 degrees C of 2. (PMID 10527934) | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Structure | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Synonyms: |
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Chemical Formula: | C6H10O6 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Weight: | Average: 178.14 Monoisotopic: 178.047738052 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
InChI Key: | WPAMZTWLKIDIOP-NQXXGFSBSA-N | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
InChI: | InChI=1S/C6H10O6/c7-2-5(10)3(8)1-4(9)6(11)12/h3,5,7-8,10H,1-2H2,(H,11,12)/t3-,5-/m1/s1 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
CAS number: | 17510-99-5 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
IUPAC Name: | (4S,5R)-4,5,6-trihydroxy-2-oxohexanoic acid | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Traditional IUPAC Name: | 2-dehydro-3-deoxy-D-gluconate | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
SMILES: | OC[C@@H](O)[C@H](O)CC(=O)C(O)=O | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Chemical Taxonomy | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Description | belongs to the class of organic compounds known as medium-chain keto acids and derivatives. These are keto acids with a 6 to 12 carbon atoms long side chain. | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Kingdom | Organic compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Super Class | Organic acids and derivatives | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Class | Keto acids and derivatives | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Sub Class | Medium-chain keto acids and derivatives | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Direct Parent | Medium-chain keto acids and derivatives | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Alternative Parents | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Substituents |
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Molecular Framework | Aliphatic acyclic compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
External Descriptors |
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Physical Properties | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
State: | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Charge: | -1 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Melting point: | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Experimental Properties: |
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Predicted Properties |
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Biological Properties | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Cellular Locations: | Cytoplasm | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Reactions: | D-Altronate <> 2-Keto-3-deoxy-D-gluconic acid + Water 2-Keto-3-deoxy-D-gluconic acid + Adenosine triphosphate <> 2-Keto-3-deoxy-6-phosphogluconic acid + ADP + Hydrogen ion D-Mannonate <> 2-Keto-3-deoxy-D-gluconic acid + Water Adenosine triphosphate + 2-Keto-3-deoxy-D-gluconic acid <> ADP + 2-Keto-3-deoxy-6-phosphogluconic acid 2-Keto-3-deoxy-D-gluconic acid + NAD <> (4S)-4,6-Dihydroxy-2,5-dioxohexanoate + NADH + Hydrogen ion D-Altronate > Water + 2-Keto-3-deoxy-D-gluconic acid 2-Keto-3-deoxy-D-gluconic acid + Adenosine triphosphate > Hydrogen ion + 2-Keto-3-deoxy-6-phosphogluconic acid + ADP 2-Keto-3-deoxy-D-gluconic acid D-Glyceraldehyde + Pyruvic acid D-Mannonate > Water + 2-Keto-3-deoxy-D-gluconic acid Adenosine triphosphate + 2-Keto-3-deoxy-D-gluconic acid > ADP + 2-Keto-3-deoxy-6-phosphogluconic acid 2-Keto-3-deoxy-D-gluconic acid + NAD > (4S)-4,6-Dihydroxy-2,5-dioxohexanoate + NADH D-altronate > Water + 2-Dehydro-3-deoxy-D-galactonate + 2-Keto-3-deoxy-D-gluconic acid D-altronate + D-altronate > Water + 2-Dehydro-3-deoxy-D-galactonate + 2-Keto-3-deoxy-D-gluconic acid 2-Dehydro-3-deoxy-D-galactonate + Adenosine triphosphate + 2-Keto-3-deoxy-D-gluconic acid > Hydrogen ion + 2-Keto-3-deoxy-6-phosphogluconic acid + Adenosine diphosphate + ADP | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
SMPDB Pathways: |
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KEGG Pathways: | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
EcoCyc Pathways: |
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Concentrations | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Not Available | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Spectra | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Spectra: |
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References | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
References: |
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Synthesis Reference: | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Material Safety Data Sheet (MSDS) | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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External Links: |
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Enzymes
- General function:
- Involved in 2-keto-3-deoxygluconate:hydrogen symporter activity
- Specific function:
- The 2-keto-3-deoxygluconate permease transports the degraded pectin products into the bacterial cell, where they serve as carbon and energy sources. This is a hydrogen coupled transport system
- Gene Name:
- kdgT
- Uniprot ID:
- P0A712
- Molecular weight:
- 33669
- General function:
- Involved in mannonate dehydratase activity
- Specific function:
- D-mannonate = 2-dehydro-3-deoxy-D-gluconate + H(2)O
- Gene Name:
- uxuA
- Uniprot ID:
- P24215
- Molecular weight:
- 44838
Reactions
D-mannonate = 2-dehydro-3-deoxy-D-gluconate + H(2)O. |
- General function:
- Involved in phosphotransferase activity, alcohol group as acceptor
- Specific function:
- ATP + 2-dehydro-3-deoxy-D-gluconate = ADP + 6- phospho-2-dehydro-3-deoxy-D-gluconate
- Gene Name:
- kdgK
- Uniprot ID:
- P37647
- Molecular weight:
- 33962
Reactions
ATP + 2-dehydro-3-deoxy-D-gluconate = ADP + 6-phospho-2-dehydro-3-deoxy-D-gluconate. |
- General function:
- Involved in 2-deoxy-D-gluconate 3-dehydrogenase activity
- Specific function:
- Catalyzes the reduction of 2,5-diketo-3-deoxygluconate (DKII or 4,6-dihydroxy-2,5-dioxohexanoate) into 2-keto-3- deoxygluconate (KDG or 2-dehydro-3-deoxygluconate) with a concomitant oxidation of NADH
- Gene Name:
- kduD
- Uniprot ID:
- P37769
- Molecular weight:
- 27070
Reactions
2-dehydro-3-deoxy-D-gluconate + NAD(+) = (4S)-4,6-dihydroxy-2,5-dioxohexanoate + NADH. |
- General function:
- Involved in hydro-lyase activity
- Specific function:
- D-altronate = 2-dehydro-3-deoxy-D-gluconate + H(2)O
- Gene Name:
- uxaA
- Uniprot ID:
- P42604
- Molecular weight:
- 54093
Reactions
D-altronate = 2-dehydro-3-deoxy-D-gluconate + H(2)O. |
- General function:
- cellular amino acid catabolic process
- Specific function:
- Probably involved in the degradation of homoserine lactone (HSL) or of a metabolite of HSL that signals starvation.
- Gene Name:
- rspA
- Uniprot ID:
- P38104
- Molecular weight:
- 45968
Reactions
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Transporters
- General function:
- Involved in 2-keto-3-deoxygluconate:hydrogen symporter activity
- Specific function:
- The 2-keto-3-deoxygluconate permease transports the degraded pectin products into the bacterial cell, where they serve as carbon and energy sources. This is a hydrogen coupled transport system
- Gene Name:
- kdgT
- Uniprot ID:
- P0A712
- Molecular weight:
- 33669
- General function:
- Involved in 2-keto-3-deoxygluconate:hydrogen symporter activity
- Specific function:
- The 2-keto-3-deoxygluconate permease transports the degraded pectin products into the bacterial cell, where they serve as carbon and energy sources. This is a hydrogen coupled transport system
- Gene Name:
- kdgT
- Uniprot ID:
- B1XB76
- Molecular weight:
- 33669
- General function:
- Involved in 2-keto-3-deoxygluconate:hydrogen symporter activity
- Specific function:
- The 2-keto-3-deoxygluconate permease transports the degraded pectin products into the bacterial cell, where they serve as carbon and energy sources. This is a hydrogen coupled transport system
- Gene Name:
- kdgT
- Uniprot ID:
- C5A077
- Molecular weight:
- 33669
- General function:
- Involved in transporter activity
- Specific function:
- Non-specific porin
- Gene Name:
- ompN
- Uniprot ID:
- P77747
- Molecular weight:
- 41220
- General function:
- Involved in transporter activity
- Specific function:
- Uptake of inorganic phosphate, phosphorylated compounds, and some other negatively charged solutes
- Gene Name:
- phoE
- Uniprot ID:
- P02932
- Molecular weight:
- 38922
- General function:
- Involved in transporter activity
- Specific function:
- OmpF is a porin that forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane. It is also a receptor for the bacteriophage T2
- Gene Name:
- ompF
- Uniprot ID:
- P02931
- Molecular weight:
- 39333
- General function:
- Involved in transporter activity
- Specific function:
- Forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane
- Gene Name:
- ompC
- Uniprot ID:
- P06996
- Molecular weight:
- 40368