Gluconic acid (ECMDB00625) (M2MDB000160)
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| Version | 2.0 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Creation Date | 2012-05-31 10:27:58 -0600 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Update Date | 2015-09-13 12:56:08 -0600 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Secondary Accession Numbers |
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| Identification | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Name: | Gluconic acid | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Description | Gluconic acid occurs naturally in fruit, honey and wine and is used as a food additive, an acidity regulator. It is also used in cleaning products where it helps cleaning up mineral deposits. It is a strong chelating agent, especially in alkaline solution. It chelates the anions of calcium, iron, aluminium, copper, and other heavy metals. Glucono delta lactone is a cyclic ester of D-gluconic acid. | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Structure |  | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Synonyms: |
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| Chemical Formula: | C6H12O7 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Weight: | Average: 196.1553 Monoisotopic: 196.058302738 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| InChI Key: | RGHNJXZEOKUKBD-SQOUGZDYSA-N | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| InChI: | InChI=1S/C6H12O7/c7-1-2(8)3(9)4(10)5(11)6(12)13/h2-5,7-11H,1H2,(H,12,13)/t2-,3-,4+,5-/m1/s1 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| CAS number: | 526-95-4 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| IUPAC Name: | (2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanoic acid | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Traditional IUPAC Name: | gluconate | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| SMILES: | OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Chemical Taxonomy | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Description | belongs to the class of organic compounds known as sugar acids and derivatives. Sugar acids and derivatives are compounds containing a saccharide unit which bears a carboxylic acid group. | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Kingdom | Organic compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Super Class | Organic oxygen compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Class | Organooxygen compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Sub Class | Carbohydrates and carbohydrate conjugates | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Direct Parent | Sugar acids and derivatives | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Alternative Parents |
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| Substituents |
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| Molecular Framework | Aliphatic acyclic compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| External Descriptors |
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| Physical Properties | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| State: | Solid | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Charge: | -1 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Melting point: | 113-118 °C | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Experimental Properties: |
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| Predicted Properties |
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| Biological Properties | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Cellular Locations: | Cytoplasm | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Reactions: | Ubiquinone-8 + D-Glucose + Water > Ubiquinol-8 + Gluconic acid + Hydrogen ion Adenosine triphosphate + Gluconic acid <> 6-Phosphogluconic acid + ADP + Hydrogen ion 2 -Dehydro-L-gulonate + Hydrogen ion + NADH > Gluconic acid + NAD 2 -Dehydro-L-gulonate + Hydrogen ion + NADPH > Gluconic acid + NADP 5-Keto-D-gluconate + Hydrogen ion + NADPH <> Gluconic acid + NADP Adenosine triphosphate + Gluconic acid <> ADP + 6-Phosphogluconic acid Gluconic acid + NADP <> 2-Keto-D-gluconic acid + NADPH + Hydrogen ion + 2-Dehydro-D-gluconate NADP + Gluconic acid <> Hydrogen ion + 2-Dehydro-D-gluconate + NADPH NAD(P)<sup>+</sup> + Gluconic acid <> NAD(P)H + 5-Keto-D-gluconate + Hydrogen ion Adenosine triphosphate + Gluconic acid > Hydrogen ion + ADP + 6-Phosphogluconic acid Gluconolactone + Water > Hydrogen ion + Gluconic acid 6-Phosphogluconic acid + Water > Gluconic acid + Phosphate Gluconic acid + NADP > 2-Dehydro-D-gluconate + NADPH Adenosine triphosphate + Gluconic acid > ADP + 6-Phosphogluconic acid Gluconic acid + NAD(P)(+) > 5-Keto-D-gluconate + NAD(P)H Gluconic acid + NAD + NADP <> 5-Keto-D-gluconate + NADH + NADPH + Hydrogen ion 2-Keto-L-gluconate + NADPH + Hydrogen ion + 2-Dehydro-D-gluconate + NADPH > Gluconic acid + NADP 5-Keto-D-gluconate + Hydrogen ion + NADPH + 5-Keto-D-gluconate + NADPH > NADP + Gluconic acid Gluconic acid + Adenosine triphosphate > ADP + Hydrogen ion + gluconate 6-phosphate | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| SMPDB Pathways: |
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| KEGG Pathways: | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| EcoCyc Pathways: |
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| Concentrations | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Find out more about how we convert literature concentrations. | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Spectra | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Spectra: | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| References | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| References: |
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| Synthesis Reference: | Anastassiadis, Savas; Morgunov, Igor G. Gluconic acid production. Recent Patents on Biotechnology (2007), 1(2), 167-180. | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Material Safety Data Sheet (MSDS) | Download (PDF) | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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Enzymes
- General function:
- Involved in oxidoreductase activity
- Specific function:
- Catalyzes a reversible reduction of 5-ketoglutanate to form D-gluconate. Dependent on NADP, almost inactive with NAD
- Gene Name:
- idnO
- Uniprot ID:
- P0A9P9
- Molecular weight:
- 27563
Reactions
| D-gluconate + NAD(P)(+) = 5-dehydro-D-gluconate + NAD(P)H. |
- General function:
- Involved in oxidoreductase activity, acting on CH-OH group of donors
- Specific function:
- GDH is probably involved in energy conservation rather than in sugar metabolism
- Gene Name:
- gcd
- Uniprot ID:
- P15877
- Molecular weight:
- 86747
Reactions
| D-glucose + ubiquinone = D-glucono-1,5-lactone + ubiquinol. |
- General function:
- Involved in oxidoreductase activity, acting on the CH-OH group of donors, NAD or NADP as acceptor
- Specific function:
- Catalyzes the NADPH-dependent reduction of glyoxylate and hydroxypyruvate into glycolate and glycerate, respectively. Can also reduce 2,5-diketo-D-gluconate (25DKG) to 5-keto-D- gluconate (5KDG), 2-keto-D-gluconate (2KDG) to D-gluconate, and 2- keto-L-gulonate (2KLG) to L-idonate (IA), but it is not its physiological function. Inactive towards 2-oxoglutarate, oxaloacetate, pyruvate, 5-keto-D-gluconate, D-fructose and L- sorbose. Activity with NAD is very low
- Gene Name:
- ghrB
- Uniprot ID:
- P37666
- Molecular weight:
- 35395
Reactions
| Glycolate + NADP(+) = glyoxylate + NADPH. |
| D-glycerate + NAD(P)(+) = hydroxypyruvate + NAD(P)H. |
| D-gluconate + NADP(+) = 2-dehydro-D-gluconate + NADPH. |
- General function:
- Involved in oxidoreductase activity, acting on the CH-OH group of donors, NAD or NADP as acceptor
- Specific function:
- Catalyzes the reduction of 2,3-diketo-L-gulonate in the presence of NADH, to form 3-keto-L-gulonate
- Gene Name:
- dlgD
- Uniprot ID:
- P37672
- Molecular weight:
- 36572
Reactions
| 3-dehydro-L-gulonate + NAD(P)(+) = (4R,5S)-4,5,6-trihydroxy-2,3-dioxohexanoate + NAD(P)H. |
- General function:
- Involved in shikimate kinase activity
- Specific function:
- ATP + D-gluconate = ADP + 6-phospho-D- gluconate
- Gene Name:
- idnK
- Uniprot ID:
- P39208
- Molecular weight:
- 21004
Reactions
| ATP + D-gluconate = ADP + 6-phospho-D-gluconate. |
- General function:
- Involved in shikimate kinase activity
- Specific function:
- ATP + D-gluconate = ADP + 6-phospho-D- gluconate
- Gene Name:
- gntK
- Uniprot ID:
- P46859
- Molecular weight:
- 19543
Reactions
| ATP + D-gluconate = ADP + 6-phospho-D-gluconate. |
- General function:
- Involved in oxidoreductase activity, acting on the CH-OH group of donors, quinone or similar compound as acceptor
- Specific function:
- Aldose sugar dehydrogenase with broad substrate specificity. The physiological substrate is unknown. Can oxidize glucose to gluconolactone. Can also utilize D-arabinose, L- arabinose and 2-deoxy-glucose. Has higher activity towards oligomeric sugars, such as maltose, maltotriose or cellobiose. It may function to input sugar-derived electrons into the respiratory network
- Gene Name:
- yliI
- Uniprot ID:
- P75804
- Molecular weight:
- 41054
Transporters
- General function:
- Involved in gluconate transmembrane transporter activity
- Specific function:
- Transports L-idonate, D-gluconate and 5-keto-D- gluconate, from the periplasm across the inner membrane
- Gene Name:
- idnT
- Uniprot ID:
- P39344
- Molecular weight:
- 46041
- General function:
- Involved in gluconate transmembrane transporter activity
- Specific function:
- High-affinity gluconate transporter with fairly broad specificity, including low affinity for glucuronate, several disaccharides, and some hexoses, but not glucose
- Gene Name:
- gntP
- Uniprot ID:
- P0AC94
- Molecular weight:
- 47137
- General function:
- Involved in gluconate transmembrane transporter activity
- Specific function:
- Part of the gluconate utilization system Gnt-I; low- affinity intake of gluconate
- Gene Name:
- gntU
- Uniprot ID:
- P0AC96
- Molecular weight:
- 46416
- General function:
- Involved in gluconate transmembrane transporter activity
- Specific function:
- Part of the gluconate utilization system Gnt-I; high- affinity intake of gluconate
- Gene Name:
- gntT
- Uniprot ID:
- P39835
- Molecular weight:
- 45966
- 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