L-Azetidine-2-carboxylic Acid

L-Azetidine-2-carboxylic acid is a non-proteinogenic amino acid derivative of L-proline that has been found in C. majalis and has diverse biological activities. It is toxic to a variety of bacteria, but the bacteria E. agglomerans and E. amnigenus metabolize it for use as a source of nitrogen. L-Azetidine-2-carboxylic acid induces misfolding of proteins when incorporated into the nascent polypeptide chain. It destabilizes the collagen triple helix and reduces the extracellular localization of collagen. L-Azetidine-2-carboxylic acid inhibits growth of type IV collagen-producing 450.1 murine mammary cancer cells in vitro (IC50 = 7.6 µg/ml) but is inactive in a 450.1 murine model of mammary cancer when administered at doses ranging from 12.5 to 200 mg/kg twice per day and induces liver toxicity at the highest dose. It is teratogenic to, and disrupts skeletal development in, hamster fetuses when administered to pregnant hamsters at a dose of 300 mg/kg on gestational day 11.Formal Name: (2S)-2-azetidinecarboxylic acid. CAS Number: 2133-34-8. Synonyms: A2C, Aze, L-AZC, LACA, (S)-(-)-Azetidine-2-carboxylic Acid. Molecular Formula: C4H7NO2. Formula Weight: 101.1. Purity: >95%. Formulation: (Request formulation change), A crystalline solid. Solubility: DMF: slightly soluble, PBS (pH 7.2): 1 mg/ml. SMILES: OC([C@@H]1CCN1)=O. InChi Code: InChI=1S/C4H7NO2/c6-4(7)3-1-2-5-3/h3,5H,1-2H2,(H,6,7)/t3-/m0/s1. InChi Key: IADUEWIQBXOCDZ-VKHMYHEASA-N. Origin: Synthetic.