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| Names | |
|---|---|
| Preferred IUPAC name
Piperidine-2-carboxylic acid | |
| Identifiers | |
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3D model (JSmol)
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| ChEBI | |
| ChemSpider | |
| ECHA InfoCard | 100.007.835 |
| EC Number |
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| KEGG | |
| MeSH | C031345 |
PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| 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.
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Transcription
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
- ^ 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.
- ^ 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.
- ^ 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.
- ^ 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.
- ^ 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.
- ^ 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.
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This page was last edited on 3 April 2024, at 23:18