CAS 2517-04-6: (±)-2-Azetidinecarboxylic acid

Azetidine-2-carboxylic acid

Applications D,L-Azetidine-2-carboxylic Acid-d4 is the isotope labelled analog of D,L-Azetidine-2-carboxylic Acid (A812490); a four-membered ring analog of L-Proline and a useful intermediate in the synthesis of polypeptides. References Barber, M., et al.: Int. J. Pept. Protein Res., 14(3), 247 (1979); Tsai., F.H., et al.: Biopolymers, 30(11-12), 1039 (1990)

Azetidine-2-carboxylic acid

This Thermo Scientific Chemicals brand product was originally part of the Acros Organics product portfolio. Some documentation and label information may refer to the legacy brand. The original Acros Organics product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.

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Azetidine-2-carboxylic acid is a non-protein amino acid that inhibits the activity of enzymes in the arginine biosynthesis pathway. It has been shown to be a potent inhibitor of human protein gene transcription and collagen synthesis. Azetidine-2-carboxylic acid is an analog of arginine, but it is not used as an amino acid in protein synthesis because it cannot be converted to urea and therefore cannot be excreted. This molecule is also found in food sources such as plants and animal tissues. In humans, azetidine-2-carboxylic acid has been shown to inhibit the production of inflammatory cytokines by inhibiting receptor activity for proinflammatory cytokines such as tumor necrosis factor alpha (TNFα).

Non-proteinogenic amino acid, similar to proline, found in beets; misincorporated in proteins, toxic and teratogenic.

Applications D,L-Azetidine-2-carboxylic Acid-d5 is a useful synthetic intermediate.