Pipecolic acid

Chemical compound From Wikipedia, the free encyclopedia

Pipecolic acid

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-amino acids, pipecolic acid is chiral, although the S-stereoisomer is more common. It is a colorless solid.

Quick Facts Names, Identifiers ...
Pipecolic acid
Thumb
Names
Preferred IUPAC name
Piperidine-2-carboxylic acid
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.007.835
EC Number
  • 217-024-4
KEGG
MeSH C031345
UNII
  • InChI=1S/C6H11NO2/c8-6(9)5-3-1-2-4-7-5/h5,7H,1-4H2,(H,8,9) N
    Key: HXEACLLIILLPRG-UHFFFAOYSA-N N
  • InChI=1/C6H11NO2/c8-6(9)5-3-1-2-4-7-5/h5,7H,1-4H2,(H,8,9)
    Key: HXEACLLIILLPRG-UHFFFAOYAL
  • C1CCNC(C1)C(=O)O
Properties
C6H11NO2
Molar mass 129.15704
Appearance white or colorless solid
Melting point 268 °C (514 °F; 541 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Close

Its biosynthesis starts from lysine.[1] CRYM, a taxon-specific protein that also binds thyroid hormones, is involved in the pipecolic acid pathway.

Medicine

It accumulates in pipecolic acidemia. Elevation of pipecolic acid can be associated with some forms of epilepsy, such as pyridoxine-dependent epilepsy.[2][3]

Occurrence and reactions

Like most amino acids, pipecolic acid is a chelating agent. One complex is Cu(HNC5H9CO2)2(H2O)2.[4]

Pipecolic acid was identified in the Murchison meteorite.[5] It also occurs in the leaves of the genus Myroxylon, a tree from South America.[6]

See also

References

Loading related searches...

Wikiwand - on

Seamless Wikipedia browsing. On steroids.