Stizolobic acid
| Names | |
|---|---|
| IUPAC name
4-[(2S)-2-amino-3-hydroxy-3-oxo-propyl]-6-oxo-pyran-2-carboxylic acid
| |
| Systematic IUPAC name
4-[(2S)-2-amino-3-hydroxy-3-oxo-propyl]-6-oxo-pyran-2-carboxylic acid | |
| Identifiers | |
3D model (JSmol)
|
|
| ChemSpider | |
| KEGG | |
PubChem CID
|
|
| UNII | |
CompTox Dashboard (EPA)
|
|
| |
| |
| Properties | |
| C9H9NO6 | |
| Molar mass | 227.172 g·mol−1 |
| Density | 1.604 g/cm3 |
| Melting point | 304.65 °C (580.37 °F; 577.80 K) |
| Boiling point | 528.25 °C (982.85 °F; 801.40 K) at 760 mmHg |
| 2.634e+005 mg/L | |
| Vapor pressure | 1.44E-12 mmHg |
| Hazards | |
| Flash point | 273.2 °C (523.8 °F; 546.3 K) |
| Related compounds | |
Other anions
|
stizolobinic acid |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
| |
Stizolobic acid is an amino acid found in the sap epicotyl tips of etiolated seedlings of Stizolobium hassjoo - Mucuna pruriens.[1]
Biosynthesis
Stizolobium hassjoo contains the enzyme stizolobate synthase which catalyzes the conversion of L-DOPA into stizolobic acid in the presence of oxidised nicotinamide adenine dinucleotide as a cofactor, under aerobic conditions.
The initial product is 4-(L-alanin-3-yl)-2-hydroxy-cis,cis-muconate 6-semialdehyde.[2]
The intermediate readily cyclises and further oxidises, forming a 2-pyrone ring; this is stizolobic acid, which is the product that is isolated and after which this enzyme is named.[3][4]
A separate enzyme, stizolobinate synthase also present in higher plants cleaves L-DOPA in a way which produces the isomeric compound, stizolobinic acid.[4]
References
- ^ Hattori, S.; Komamine, A. (1959). "Stizolobic Acid: a New Amino-Acid in Stizolobium hassjoo". Nature. 183 (4668): 1116. Bibcode:1959Natur.183.1116H. doi:10.1038/1831116a0. S2CID 4219696.
- ^ Enzyme 1.13.11.29 at KEGG Pathway Database.
- ^ Saito, Koshi; Komamine, Atsushi (1976). "Biosynthesis of Stizolobinic Acid and Stizolobic Acid in Higher Plants. An Enzyme System(s) Catalyzing the Conversion of Dihydroxyphenylalanine into Stizolobinic Acid and Stizolobic Acid from Etiolated Seedlings of Stizolobium hassjoo". European Journal of Biochemistry. 68 (1): 237–243. doi:10.1111/j.1432-1033.1976.tb10783.x. PMID 9285.
- ^ a b Saito, Koshi; Komamine, Atsushi (1978). "Biosynthesis of Stizolobinic Acid and Stizolobic Acid in Higher Plants". European Journal of Biochemistry. 82 (2): 385–392. doi:10.1111/j.1432-1033.1978.tb12033.x. PMID 624278.