Cyanoalanine

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| ImageFile = 3-Cyano-L-alanine.svg

| ImageSize = 200px

| ImageAlt =

| IUPACName = (2S)-2-Amino-3-cyanopropanoic acid

| OtherNames = 3-Cyano-L-alanine
β-Cyanoalanine
3-Cyanoalanine

|Section1={{Chembox Identifiers

| CASNo = 6232-19-5

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

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

| UNII = B75AJA4DCJ

| PubChem = 439742

| ChemSpiderID = 388802

| KEGG = C02512

| ChEBI = 132546

| 3DMet = B01594

| StdInChI=1S/C4H6N2O2/c5-2-1-3(6)4(7)8/h3H,1,6H2,(H,7,8)/t3-/m0/s1

| InChIKey = BXRLWGXPSRYJDZ-VKHMYHEASA-N

| SMILES = C(C#N)C(C(=O)O)N}}

|Section2={{Chembox Properties

| C=4|H=6|N=2|O=2

| Appearance = White solid

| Density =

| MeltingPt =

| BoilingPt =

| Solubility = }}

|Section3={{Chembox Hazards

| MainHazards =

| FlashPt =

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Cyanoalanine (more accurately β-Cyano-L-alanine) is an amino acid with the formula NCCH₂CH(NH₂)CO₂H. Like most amino acids, it exists as a tautomer NCCH₂CH(NH₃⁺)CO₂⁻. It is a rare example of a nitrile-containing amino acid. It is a white, water-soluble solid. It can be found in common vetch seeds.

Cyanoalanine arises in nature by the action of cyanide on cysteine catalyzed by L-3-cyanoalanine synthase:{{cite journal|title=Enzymatic mechanism and biochemistry for cyanide degradation: A review|author1=Gupta, Neha |author2=Balomajumder, Chandrajit |author3=Agarwal, V. K. |journal=Journal of Hazardous Materials| year=2010|volume =176|issue=1–3|pages=1–13|doi=10.1016/j.jhazmat.2009.11.038|pmid=20004515}}

:HSCH₂CH(NH₂)CO₂H + HCN → NCCH₂CH(NH₂)CO₂H + H₂S

It is converted to aspartic acid and asparagine enzymatically.