Imino acid

In chemistry, an imino acid is any molecule that contains both imine (>C=NH) and carboxyl (-C(=O)-OH) functional groups.[1]

Imino group attached to carbon
Carboxylic acid
The two functional groups that together define an imino acid
1-Pyrroline-5-carboxylic acid, an N-substituted imino acid

Imino acids are related to amino acids, which contain both amino (-NH2) and carboxyl (-COOH) functional groups, differing in the bonding to the nitrogen.

The D-amino acid oxidase enzymes are able to convert amino acids into imino acids. Also the direct biosynthetic precursor to the amino acid proline is the imino acid (S)-Δ1-pyrroline-5-carboxylate (P5C).

proline

Amino acids containing a secondary amine group (the only proteinogenic amino acid of this type is proline) are sometimes named imino acids,[2][3] though this usage is obsolescent.[1]

The term imino acid is also the obsolete term for imidic acids, containing the -C(=NH)-OH group, and should not be used for them.[1]

References
  1. IUPAC, Compendium of Chemical Terminology, 2nd ed. (the "Gold Book") (1997). Online corrected version:  (2006–) "Imino acids". doi:10.1351/goldbook.I02959
  2. Proline at the US National Library of Medicine Medical Subject Headings (MeSH)
  3. "Archived copy". Archived from the original on 2008-01-18. Retrieved 2015-01-03.CS1 maint: archived copy as title (link)
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