Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | L-Alanine | HCID 5950 | — |
| Reactant | L-(-)-Ornithine | HCID 6262 | — |
| Reactant | acetyl CoA | HCID 444493 | — |
| Reactant | Acetylpyruvate | HCID 5459760 | — |
| Reactant | HCID 11083863 | HCID 11083863 | — |
| Reactant | Penta-2,4-dienoate | HCID 73155734 | — |
| Product | Acetylpyruvate | HCID 5459760 | — |
| Product | 4-Hydroxy-2-oxopentanoate | HCID 9543038 | — |
| Product | HCID 20514168 | HCID 20514168 | — |
Reaction Steps
FIG. 13 shows pathways from alanine or ornithine to 2,4-pentadienoate. In Step A of FIG. 13, alanine and acetyl-CoA are joined by AKP thiolase to form AKP. In one pathway, AKP is deaminated to acetylacrlate (Step B). The 4-oxo group of acetylacrylate is then reduced and dehydrated to 2,4-pentadienoate (Steps C/D). In an alternative pathway, AKP is converted to 2,4-dioxopentanoate by an aminotransferase or dehydrogenase (Step E). Reduction of the 2- or 4-oxo group of 2,4-dioxopentanoate yields 2-hydroxy-4-oxopentanoate (Step H) or 4-hydroxy-2-oxovalerate (Step K), respectively. 4-Hydroxy-2-oxovalerate can alternately be formed by the reduction of AKP to 2-amino-4-hydroxypentanoate (Step J) followed by transamination or oxidative deamination (Step L). Once formed, 4-hydroxy-2-oxovalerate can be converted to 2,4-pentadienoate in three enzymatic steps as shown in FIG. 12 (Steps B/C/D of FIG. 12). The 2-hydroxy-4-oxopentanoate intermediate can undergo dehydration to acetylacrylate (Step F) followed by reduction and dehydration (Steps C/D).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08715957B2 |
|---|
| Source dataset | uspto-grants-2014_05 |
|---|
| ORD ID | ord-a9e81385edd246a0915772614e6330c8 |
|---|
| Source note | uspto-grants-2014_05 |
|---|