Pipecolic acid

Pipecolic acid (piperidine-2-carboxylic acid) is a small organic molecule which accumulates in pipecolic acidemia. It is a carboxylic acid of piperidine.

Pipecolic acid

Names
IUPAC name piperidine-2-carboxylic acid
Identifiers
CAS Number	3105-95-1 (2S)
3D model (JSmol)	Interactive image
ChEBI	CHEBI:17964
ChemSpider	826
ECHA InfoCard	100.007.835
EC Number	217-024-4
KEGG	C00408
MeSH	C031345
PubChem CID	849
UNII	69374CKB33
CompTox Dashboard (EPA)	DTXSID40862144
InChI InChI=1S/C6H11NO2/c8-6(9)5-3-1-2-4-7-5/h5,7H,1-4H2,(H,8,9) Key: HXEACLLIILLPRG-UHFFFAOYSA-N InChI=1/C6H11NO2/c8-6(9)5-3-1-2-4-7-5/h5,7H,1-4H2,(H,8,9) Key: HXEACLLIILLPRG-UHFFFAOYAL
SMILES C1CCNC(C1)C(=O)O
Properties
Chemical formula	C6H11NO2
Molar mass	129.15704
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Biochemical effects

Pipecolic acid can be associated with some forms of epilepsy.[1]

CRYM, a taxon-specific crystallin protein that also binds thyroid hormones, is involved in the pipecolic acid pathway.

Environmental abundance and relevance

Pipecolic acid was identified in the Murchison meteorite.[2] It also occurs in the leaves of the genus Myroxylon, a tree from South America.[3]

Stereochemistry

Pipecolic acid, like many other α-amino acids, has a chiral stereocenter at the α carbon.

See also

• Bupivacaine

References

1. Plecko B, Hikel C, Korenke GC, et al. (2005). "Pipecolic acid as a diagnostic marker of pyridoxine-dependent epilepsy". Neuropediatrics. 36 (3): 200–5. doi:10.1055/s-2005-865727. PMID 15944906.
2. Kvenholden, Keith A.; Lawless, James G.; Ponnamperuma, Cyril (February 1971). "Nonprotein Amino Acids in the Murchison Meteorite". Proceedings of the National Academy of Sciences. 68 (2): 486–490. Bibcode:1971PNAS...68..486K. doi:10.1073/pnas.68.2.486. PMC 388966. PMID 16591908.
3. Kite, GC; Cardoso, D; Lewis, GP; Zartman, CE; de Queiroz, LP; Veitch, NC (2015). "Monomethyl ethers of 4,5-dihydroxypipecolic acid from Petaladenium urceoliferum: Enigmatic chemistry of an enigmatic legume". Phytochemistry. 116: 198–202. doi:10.1016/j.phytochem.2015.02.026. PMID 25817832.