Azetidinecarboxylic acids

Acetidine carboxylic acids are among the cyclic non-proteinogenic amino acids . Depending on the position of the carboxy group on the azetidine ring, a distinction is made between azetidine-2-carboxylic acids and azetidine-3-carboxylic acid (CAS number: 36476-78-5). The azetidine-2-carboxylic acid has a stereogenic center and is therefore chiral . Thus there are two enantiomers of azetidine-2-carboxylic acids , the ( S ) -azetidine-2-carboxylic acids and the ( R ) -azetidine-2-carboxylic acid:

( S ) -azetidine-2-carboxylic acid (left), ( R ) -azetidine-2-carboxylic acid (middle) and azetidine-3-carboxylic acid (right)

( S ) -azetidine-2-carboxylic acid occurs naturally in the lily family (including lily of the valley ) and in the seeds of some legumes . Because of its similarity to proline , it is incorporated into peptides instead of this amino acid , which then lose their function.

Individual evidence

1. ↑ Entry on azetidine-2-carboxylic acid. In: Römpp Online . Georg Thieme Verlag, accessed on December 29, 2014.