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Pipecolic acid
Names
Preferred IUPAC name
Piperidine-2-carboxylic acid
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.007.835 Edit this at Wikidata
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).
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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.

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

Medicine[edit]

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[edit]

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[edit]

References[edit]

  1. ^ Gatto, Gregory J.; Boyne, Michael T.; Kelleher, Neil L.; Walsh, Christopher T. (2006). "Biosynthesis of Pipecolic Acid by RapL, a Lysine Cyclodeaminase Encoded in the Rapamycin Gene Cluster". Journal of the American Chemical Society. 128 (11): 3838–3847. doi:10.1021/ja0587603. PMID 16536560.
  2. ^ 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.
  3. ^ Kaminiów K, Pająk M, Pająk R, Paprocka J (December 2021). "Pyridoxine-Dependent Epilepsy and Antiquitin Deficiency Resulting in Neonatal-Onset Refractory Seizures". Brain Sciences. 12 (1): 65. doi:10.3390/brainsci12010065. PMC 8773593. PMID 35053812.
  4. ^ Hockless, David C.R.; Mayadunne, Renuka C.; Wild, S.Bruce (1995). "Convenient resolution of (±)-piperidine-2-carboxylic acid ((±)-pipecolic acid) by separation of palladium(II) diastereomers containing orthometallated (S)-(−)-1-[1-(dimethylamino)ethyl]naphthalene". Tetrahedron: Asymmetry. 6 (12): 3031–3037. doi:10.1016/0957-4166(95)00400-9.
  5. ^ 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.
  6. ^ 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. Bibcode:2015PChem.116..198K. doi:10.1016/j.phytochem.2015.02.026. PMID 25817832.
source: https://en.wikipedia.org/wiki/Pipecolic_acid

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