Imino acid: Difference between revisions

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

Imine

Carboxylic acid

The two functional groups that together define an 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 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).

Related terminology

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

^ ^a ^b ^c IUPAC, Compendium of Chemical Terminology, 2nd ed. (the "Gold Book") (1997). Online corrected version: (2006–) "Imino acids". doi:10.1351/goldbook.I02959
^ Proline at the U.S. National Library of Medicine Medical Subject Headings (MeSH)
^ http://opbs.okstate.edu/5753/Amino%20Acids.html

External links

imino+acids at the U.S. National Library of Medicine Medical Subject Headings (MeSH)

[goldbook-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 U.S. National Library of Medicine Medical Subject Headings (MeSH)

[3] ttp://opbs.okstate.edu/5753/Amino%20Acids.html

[1]

@@ Line 23: / Line 23: @@
 [[Image:L-proline-skeletal.png|thumb|100px|[[proline]]]]
-Amino acids containing a [[amine|secondary amine]] group (the only [[proteinogenic amino acid]] of this type is [[proline]]) are sometimes named imino acids,<ref>{{MeshName|Proline}}</ref><ref>http://opbs.okstate.edu/5753/Amino%20Acids.html</ref> though this usage is disputed by some.
+Amino acids containing a [[amine|secondary amine]] group (the only [[proteinogenic amino acid]] of this type is [[proline]]) are sometimes named imino acids,<ref>{{MeshName|Proline}}</ref><ref>http://opbs.okstate.edu/5753/Amino%20Acids.html</ref> though this usage is  .
 The term imino acid is also the obsolete term for [[imidic acid]]s, containing the -C(=NH)-OH group, and should not be used for them.<ref name=goldbook/>