Name: Azetidine-3-carboxylic acid
Brand: BOC Sciences
Rating: 5 (1 reviews)

Synonyms

3-Carboxyazetidine; 3-Azetidinecarboxylic acid; CHA-811; h-aze(3)-oh; 3-azetidine carboxylic acid

IUPAC Name

azetidine-3-carboxylic acid

Canonical SMILES

C1C(CN1)C(=O)O

InChI

InChI=1S/C4H7NO2/c6-4(7)3-1-5-2-3/h3,5H,1-2H2,(H,6,7)

InChIKey

GFZWHAAOIVMHOI-UHFFFAOYSA-N

Density

1.275 g/cm3

Melting Point

> 200 °C (dec.)

Appearance

Pale yellow crystalline powder

Storage

Store at 2-8 °C

Signal Word

Warning

Boiling Point

242.0 °C at 760 mmHg

Azetidine-3-carboxylic acid is a cyclic amino acid with a unique structure that offers several promising applications in scientific research and industry. Here are some key applications of Azetidine-3-carboxylic acid:

Peptide Synthesis: Azetidine-3-carboxylic acid is utilized in the synthesis of cyclic peptides, which have enhanced stability and bioavailability compared to linear peptides. These cyclic peptides can be used in drug development to improve therapeutic properties and target specificity. By incorporating Azetidine-3-carboxylic acid, researchers can design peptides with unique structural features that are resistant to degradation.

Protein Structure Studies: The introduction of Azetidine-3-carboxylic acid into protein sequences provides a tool for studying protein folding and stability. Its rigid cyclic structure can induce conformational constraints, aiding in the examination of protein folding pathways and the identification of key stabilizing interactions. This application is crucial for understanding protein dynamics and engineering more stable protein therapeutics.

Antibacterial Research: Azetidine-3-carboxylic acid derivatives have been investigated for their potential antibacterial properties. By modifying its structure, researchers aim to develop novel antimicrobial agents that can inhibit bacterial growth and combat antibiotic-resistant strains. This application holds significant promise in addressing the growing public health concern of antibiotic resistance.

Material Science: Azetidine-3-carboxylic acid is used to create innovative materials with unique mechanical and chemical properties. Its incorporation into polymer matrices can enhance the material's thermal stability, mechanical strength, and resistance to environmental degradation. This makes it valuable for applications in the development of advanced materials for industrial and biomedical purposes.

1.Cyclooxygenase 2 inhibitor celecoxib inhibits glutamate release by attenuating the PGE2/EP2 pathway in rat cerebral cortex endings.

Lin TY1, Lu CW1, Wang CC1, Huang SK1, Wang SJ2. J Pharmacol Exp Ther. 2014 Oct;351(1):134-45. doi: 10.1124/jpet.114.217372. Epub 2014 Jul 21.

The excitotoxicity caused by excessive glutamate is a critical element in the neuropathology of acute and chronic brain disorders. Therefore, inhibition of glutamate release is a potentially valuable therapeutic strategy for treating these diseases. In this study, we investigated the effect of celecoxib, a selective cyclooxygenase-2 (COX-2) inhibitor that reduces the level of prostaglandin E2 (PGE2), on endogenous glutamate release in rat cerebral cortex nerve terminals (synaptosomes). Celecoxib substantially inhibited the release of glutamate induced by the K(+) channel blocker 4-aminopyridine (4-AP), and this phenomenon was prevented by chelating the extracellular Ca(2+) ions and by the vesicular transporter inhibitor bafilomycin A1. Celecoxib inhibited a 4-AP-induced increase in cytosolic-free Ca(2+) concentration, and the celecoxib-mediated inhibition of glutamate release was prevented by the Cav2.2 (N-type) and Cav2.1 (P/Q-type) channel blocker ω-conotoxin MVIIC.

2.Structures of (S)-(-)-4-oxo-2-azetidinecarboxylic acid and 3-azetidinecarboxylic acid from powder synchrotron diffraction data.

Mora AJ1, Brunelli M, Fitch AN, Wright J, Báez ME, López-Carrasquero F. Acta Crystallogr B. 2006 Aug;62(Pt 4):606-11. Epub 2006 Jul 12.

The crystal structures of the four-membered heterocycles (S)-(-)-4-oxo-2-azetidinecarboxylic acid (I) and 3-azetidinecarboxylic acid (II) were solved by direct methods using powder synchrotron X-ray diffraction data. The asymmetry of the oxoazetidine and azetidine rings is discussed, along with the hydrogen bonding.