Secondary amino acid

In organic chemistry, secondary amino acids are amino acids which do not contain the amino group −NH2 but are rather a secondary amine (>NH). Secondary amino acids can be classified to cyclic acids, such as proline, and acyclic N-substituted amino acids.

In nature, proline, hydroxyproline, pipecolic acid and sarcosine are well-known secondary amino acids. Proline is the only proteinogenic secondary amino acid; all other secondary amino acids are non-proteinogenic. Hydroxyproline is incorporated into proteins by hydroxylation of proline. Pipecolic acid, a heavier analog of proline, is found in efrapeptin. Sarcosine is a N-methylated glycine in which the methyl group is used in many biochemical reactions. Azetidine-2-carboxylic acid is a smaller homolog of proline that is found in plants.

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