Azetidine-2-carboxylic acid
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-Azetidine-2-carboxylic_acid-Structural_formula_V1.svg) | |
| Names | |
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| IUPAC name
Azetidine-2-carboxylic acid | |
| Identifiers | |
3D model (JSmol) |
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| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.016.693 |
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| KEGG | |
PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| Properties | |
| C4H7NO2 | |
| Molar mass | 101.104 g/mol |
| Appearance | crystalline solid |
| Density | 1.275 g/cm3 |
| Melting point | 215 °C (419 °F; 488 K) |
| Boiling point | 242 °C (468 °F; 515 K) |
| 5.0 g/100 ml | |
| Hazards | |
| Flash point | 100.1 °C (212.2 °F; 373.2 K) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Azetidine-2-carboxylic acid (abbreviated Aze or Azc) is a plant non-protein amino acid homologue of proline with the molecular formula C4H7NO2. Aze is a heterocyclic, 4 membered ring with nitrogen as its heteroatom (an azetidine), and a carboxylic acid group substituted on one of the ring carbon atoms. The main difference between Aze and proline is the ring of Aze has four members and the ring of proline has five.[2] Aze has the ability to act as an analog of proline and can be incorporated into proteins in place of proline.
Optically inactive Aze was obtained in small yield from the neurotransmitter GABA by α-bromination, followed by removal of hydrogen bromide from the intermediate γ-amino-α-bromobutyric acid and ring closure by treatment with a barium hydroxide solution. An optically active Aze was obtained by treatment of α,γ-diaminobutyric acid dihydrochloride with a mixture of nitrous and hydrochloric acids to yield γ-amino-α-chlorobutyric acid, followed by elimination of hydrogen chloride and cyclization by treatment with barium hydroxide.[3]
