Glyceric acid (ECMDB04077) (M2MDB000597)
| Record Information | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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| Version | 2.0 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Creation Date | 2012-05-31 14:04:17 -0600 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Update Date | 2015-09-13 12:56:13 -0600 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Secondary Accession Numbers |
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| Identification | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Name: | Glyceric acid | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Description | Glyceric acid is a colorless syrupy acid, obtained from oxidation of glycerol. It is a natural three-carbon sugar acid. Salts and esters of glyceric acid are known as glycerates. Several phosphate derivatives of glyceric acid, including 2-phosphoglyceric acid, 3-phosphoglyceric acid, 2,3-bisphosphoglyceric acid, and 1,3-bisphosphoglyceric acid, are important biochemical intermediates. (Wikipedia) | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Structure |  | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Synonyms: |
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| Chemical Formula: | C3H6O4 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Weight: | Average: 106.0773 Monoisotopic: 106.02660868 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| InChI Key: | RBNPOMFGQQGHHO-UWTATZPHSA-N | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| InChI: | InChI=1S/C3H6O4/c4-1-2(5)3(6)7/h2,4-5H,1H2,(H,6,7)/t2-/m1/s1 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| CAS number: | 473-81-4 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| IUPAC Name: | (2R)-2,3-dihydroxypropanoic acid | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Traditional IUPAC Name: | glycerate | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| SMILES: | OC[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 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Substituents |
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| Molecular Framework | Aliphatic acyclic compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| External Descriptors |
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| Physical Properties | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| State: | Liquid | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Charge: | -1 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Melting point: | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Experimental Properties: |
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| Predicted Properties |
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| Biological Properties | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Cellular Locations: | Cytoplasm | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Reactions: | Tartronate semialdehyde + Hydrogen ion + NADH <> Glyceric acid + NAD Hydrogen ion + Hydroxypyruvic acid + NADH > Glyceric acid + NAD Hydrogen ion + Hydroxypyruvic acid + NADPH > Glyceric acid + NADP Adenosine triphosphate + Glyceric acid > 3-Phosphoglycerate + ADP + Hydrogen ion Water + 2(alpha-D-Mannosyl-6-phosphate)-D-glycerate > Glyceric acid + Mannose 6-phosphate Adenosine triphosphate + Glyceric acid > 2-Phospho-D-glyceric acid + ADP + Hydrogen ion Glyceric acid + NAD <> Hydroxypyruvic acid + NADH + Hydrogen ion Glyceric acid + NADP <> Hydroxypyruvic acid + NADPH + Hydrogen ion Adenosine triphosphate + Glyceric acid <> ADP + 3-Phospho-D-glycerate Glyceric acid + NAD <> Tartronate semialdehyde + NADH + Hydrogen ion Glyceric acid + NADP <> Tartronate semialdehyde + NADPH + Hydrogen ion Tartaric acid <> Glyceric acid + Carbon dioxide NAD(P)<sup>+</sup> + Glyceric acid < NAD(P)H + Tartronate semialdehyde + Hydrogen ion Glyceric acid + NAD(P)(+) > Tartronate semialdehyde + NAD(P)H Glyceric acid + NAD(P)(+) > Hydroxypyruvic acid + NAD(P)H Adenosine triphosphate + Glyceric acid > ADP + 2-Phospho-D-glyceric acid Adenosine triphosphate + Glyceric acid > ADP + 3-Phospho-D-glycerate 2-O-(6-Phospho-alpha-D-mannosyl)-D-glycerate + Water > Mannose 6-phosphate + Glyceric acid Glyceric acid + NAD + NADP <> Tartronate semialdehyde + NADH + NADPH + Hydrogen ion 2(alpha-D-Mannosyl-6-phosphate)-D-glycerate + Water <> Mannose 6-phosphate + Glyceric acid Tartronate semialdehyde + Hydrogen ion + NADPH + NADPH > NADP + Glyceric acid Glyceric acid + Adenosine triphosphate > Hydrogen ion + Adenosine diphosphate + 2-Phosphoglyceric acid + ADP + 2-Phosphoglyceric acid Glyceric acid + Adenosine triphosphate > Adenosine diphosphate + Hydrogen ion + 3-Phosphoglyceric acid + ADP + 3-Phosphoglycerate Tartronate semialdehyde + NADH + Hydrogen ion > NAD + Glyceric acid 2-O-(6-Phospho-alpha-D-mannosyl)-D-glycerate + Water > Mannose 6-phosphate + Glyceric acid Adenosine triphosphate + Glyceric acid <> ADP +3 3-Phospho-D-glycerate More...Adenosine triphosphate + Glyceric acid > ADP +3 3-Phospho-D-glycerate Tartronate semialdehyde + Hydrogen ion + NADH <> Glyceric acid + NAD Hydrogen ion + Hydroxypyruvic acid + NADH > Glyceric acid + NAD Adenosine triphosphate + Glyceric acid <> ADP +3 3-Phospho-D-glycerate | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| 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: | Kyriacou, Demetrios; Tougas, Terrence P. Preparation of glyceric acid by anodic oxidation of glycerol at a silver oxide electrode. Journal of Organic Chemistry (1987), 52(11), 2318-19. | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Material Safety Data Sheet (MSDS) | Download (PDF) | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Links | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| External Links: |
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Enzymes
- General function:
- Involved in 3-hydroxyisobutyrate dehydrogenase activity
- Specific function:
- (R)-glycerate + NAD(P)(+) = 2-hydroxy-3- oxopropanoate + NAD(P)H
- Gene Name:
- garR
- Uniprot ID:
- P0ABQ2
- Molecular weight:
- 30427
Reactions
| D-glycerate + NAD(P)(+) = 2-hydroxy-3-oxopropanoate + NAD(P)H. |
- General function:
- Involved in glycerate kinase activity
- Specific function:
- ATP + (R)-glycerate = ADP + 3-phospho-(R)- glycerate
- Gene Name:
- garK
- Uniprot ID:
- P23524
- Molecular weight:
- 39104
Reactions
| ATP + (R)-glycerate = ADP + 3-phospho-(R)-glycerate. |
- 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 NADPH-dependent reduction of glyoxylate and hydroxypyruvate into glycolate and glycerate, respectively. Inactive towards 2-oxo-D-gluconate, 2-oxoglutarate, oxaloacetate and pyruvate. Only D- and L-glycerate are involved in the oxidative activity with NADP. Activity with NAD is very low
- Gene Name:
- ghrA
- Uniprot ID:
- P75913
- Molecular weight:
- 35343
Reactions
| Glycolate + NADP(+) = glyoxylate + NADPH. |
| D-glycerate + NAD(P)(+) = hydroxypyruvate + NAD(P)H. |
- General function:
- Involved in magnesium ion binding
- Specific function:
- Catalyzes the NAD(+)-dependent oxidative decarboxylation of D-malate into pyruvate. Is essential for aerobic growth on D- malate as the sole carbon source. But is not required for anaerobic D-malate utilization, although DmlA is expressed and active in those conditions. Appears to be not able to use L- tartrate as a substrate for dehydrogenation instead of D-malate
- Gene Name:
- dmlA
- Uniprot ID:
- P76251
- Molecular weight:
- 40315
Reactions
| (R)-malate + NAD(+) = pyruvate + CO(2) + NADH. |
- General function:
- Involved in 3-hydroxyisobutyrate dehydrogenase activity
- Specific function:
- (R)-glycerate + NAD(P)(+) = 2-hydroxy-3- oxopropanoate + NAD(P)H
- Gene Name:
- glxR
- Uniprot ID:
- P77161
- Molecular weight:
- 30800
Reactions
| D-glycerate + NAD(P)(+) = 2-hydroxy-3-oxopropanoate + NAD(P)H. |
- General function:
- Involved in glycerate kinase activity
- Specific function:
- ATP + (R)-glycerate = ADP + 3-phospho-(R)- glycerate
- Gene Name:
- glxK
- Uniprot ID:
- P77364
- Molecular weight:
- 38734
Reactions
| ATP + (R)-glycerate = ADP + 3-phospho-(R)-glycerate. |
- General function:
- Involved in catalytic activity
- Specific function:
- May hydrolyze mannosyl-D-glycerate to mannose-6- phosphate and glycerate
- Gene Name:
- mngB
- Uniprot ID:
- P54746
- Molecular weight:
- 100014
Reactions
| 2-O-(6-phospho-alpha-D-mannosyl)-D-glycerate + H(2)O = D-mannose 6-phosphate + D-glycerate. |
Transporters
- General function:
- Involved in transporter activity
- Specific function:
- Uptake of D-glucarate
- Gene Name:
- gudP
- Uniprot ID:
- Q46916
- Molecular weight:
- 49142
- General function:
- Involved in transporter activity
- Specific function:
- Uptake of D-galactarate
- Gene Name:
- garP
- Uniprot ID:
- P0AA80
- Molecular weight:
- 49009
- 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