:Stizolobic acid

{{chembox

| ImageFile =Stizolobic acid.svg

| IUPACName = 4-[(2S)-2-amino-3-hydroxy-3-oxo-propyl]-6-oxo-pyran-2-carboxylic acid

| SystematicName = 4-[(2S)-2-amino-3-hydroxy-3-oxo-propyl]-6-oxo-pyran-2-carboxylic acid

| OtherNames =

|Section1={{Chembox Identifiers

| Abbreviations =

| CASNo = 15911-87-2

| CASNo_Ref = {{cascite|correct|CAS}}

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = QXP0P9096P

| PubChem = 161158

| KEGG = C06047

| SMILES = c1c(cc(=O)oc1C(=O)O)C[C@@H](C(=O)O)N

| InChI = InChI=1/C9H9NO6/c10-5(8(12)13)1-4-2-6(9(14)15)16-7(11)3-4/h2-3,5H,1,10H2,(H,12,13)(H,14,15)/t5-/m0/s1

| ChemSpiderID =141574}}

|Section2={{Chembox Properties

| Formula = | C=9 | H=9 | N=1 | O=6

| Appearance =

| Density = 1.604 g/cm3

| MeltingPtC = 304.65

| MeltingPt_notes =

| BoilingPtC = 528.25

| BoilingPt_notes = at 760 mmHg

| Solubility = 2.634e+005 mg/L

| SolubleOther =

| Solvent =

| LogP =

| VaporPressure = 1.44E-12 mmHg

| HenryConstant =

| AtmosphericOHRateConstant =

| pKa =

| pKb = }}

|Section7={{Chembox Hazards

| ExternalSDS =

| MainHazards =

| NFPA-H =

| NFPA-F =

| NFPA-R =

| NFPA-S =

| HPhrases =

| PPhrases =

| GHS_ref =

| FlashPtC = 273.2

| AutoignitionPtC =

| ExploLimits =

| LD50 =

| PEL = }}

|Section8={{Chembox Related

| OtherAnions = stizolobinic acid

| OtherCations =

| OtherFunction =

| OtherFunction_label =

| OtherCompounds = }}

}}

Stizolobic acid is an amino acid found in the sap epicotyl tips of etiolated seedlings of Stizolobium hassjoo - Mucuna pruriens.{{cite journal | doi = 10.1038/1831116a0 | title = Stizolobic Acid: a New Amino-Acid in Stizolobium hassjoo | year = 1959 | last1 = Hattori | first1 = S. | last2 = Komamine | first2 = A. | journal = Nature | volume = 183 | issue = 4668 | pages = 1116| bibcode = 1959Natur.183.1116H | s2cid = 4219696 }}

Biosynthesis

Stizolobium hassjoo catalyzes the conversion of L-dihydroxyphenylalanine into stizolobinic acid, alpha-amino-6-carboxy-2-oxo-2H-pyran-3-propionic acid, and stizolobic acid, alpha-amino-6-carboxy-2-oxo-2H-pyran-4-propionic acid, in the presence of NADP+ or NAD+ under aerobic conditions.

References