Pipecolic acid

 ( Alpha-amino Acids ) 

Pipecolic acid (piperidine-2-carboxylic acid) is an organic compound with the formula HNC₅H₉CO₂H. It is a carboxylic acid derivative of piperidine and, as such, an amino acid, although not one encoded genetically. Like many other α-, pipecolic acid is chiral, although the S-stereoisomer is more common. It is a colorless solid.

Its biosynthesis starts from lysine. CRYM, a taxon-specific protein that also binds , is involved in the pipecolic acid pathway.

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Medicine It accumulates in pipecolic acidemia. Elevation of pipecolic acid can be associated with some forms of epilepsy, such as pyridoxine-dependent epilepsy.

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Occurrence and reactions Like most amino acids, pipecolic acid is a chelating agent. One complex is Cu(HNC₅H₉CO₂)₂(H₂O)₂.

Pipecolic acid was identified in the Murchison meteorite. It also occurs in the leaves of the genus Myroxylon, a tree from South America.

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See also

• Bupivacaine
• Efrapeptin

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