Pipecolic acid

Pipecolic acid
Names
IUPAC name
piperidine-2-carboxylic acid
Identifiers
3105-95-1 YesY
3D model (Jmol) Interactive image
ChEBI CHEBI:17964 N
ChemSpider 826 N
ECHA InfoCard 100.019.511
EC Number 217-024-4
KEGG C00408 N
MeSH C031345
PubChem 849
Properties
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

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

Biochemical effects

It 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]

Stereochemistry

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

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. doi:10.1073/pnas.68.2.486. PMC 388966Freely accessible. PMID 16591908.

See also


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