Pipecolic acid (piperidine-2-carboxylic acid) is an organic compound with the formula HNC
5H
9CO
2H. It is a carboxylic acid derivative of
piperidine
Piperidine is an organic compound with the molecular formula (CH2)5NH. This heterocyclic amine consists of a six-membered ring containing five methylene bridges (–CH2–) and one amine bridge (–NH–). It is a colorless liquid with an odor de ...
and, as such, an
amino acid
Amino acids are organic compounds that contain both amino and carboxylic acid functional groups. Although over 500 amino acids exist in nature, by far the most important are the 22 α-amino acids incorporated into proteins. Only these 22 a ...
, although not one encoded genetically. Like many other
α-
amino acid
Amino acids are organic compounds that contain both amino and carboxylic acid functional groups. Although over 500 amino acids exist in nature, by far the most important are the 22 α-amino acids incorporated into proteins. Only these 22 a ...
s, pipecolic acid is chiral, although the S-stereoisomer is more common. It is a colorless solid.
Its biosynthesis starts from
lysine
Lysine (symbol Lys or K) is an α-amino acid that is a precursor to many proteins. Lysine contains an α-amino group (which is in the protonated form when the lysine is dissolved in water at physiological pH), an α-carboxylic acid group ( ...
.
CRYM, a taxon-specific protein that also binds
thyroid hormone
File:Thyroid_system.svg, upright=1.5, The thyroid system of the thyroid hormones triiodothyronine, T3 and T4
rect 376 268 820 433 Thyroid-stimulating hormone
rect 411 200 849 266 Thyrotropin-releasing hormone
rect 297 168 502 200 Hypothalamus
r ...
s, 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
Epilepsy is a group of Non-communicable disease, non-communicable Neurological disorder, neurological disorders characterized by a tendency for recurrent, unprovoked Seizure, seizures. A seizure is a sudden burst of abnormal electrical activit ...
, such as
pyridoxine-dependent epilepsy
Pyridoxine-dependent epilepsy (PDE) is a rare genetic disorder characterized by intractable seizures in the prenatal and neonatal period. The disorder was first recognized in the 1950s, with the first description provided by Hunt et al. in 1954. ...
.
Occurrence and reactions
Like most amino acids, pipecolic acid is a chelating agent. One complex is Cu(HNC
5H
9CO
2)
2(H
2O)
2.
Pipecolic acid was identified in the
Murchison meteorite
The Murchison meteorite is a meteorite that fell in Australia in 1969 near Murchison, Victoria. It belongs to the carbonaceous chondrite class, a group of meteorites rich in organic compounds. Due to its mass (over ) and the fact that it was ...
.
It also occurs in the leaves of the genus ''
Myroxylon
''Myroxylon'' is a genus of Fabaceae native to Latin America.
History
The first described species in this genus was '' M. balsamum.'' It was originally described in 1753 by Linnaeus as ''Toluifera balsamum'', based on a specimen collected in ...
'', a tree from South America.
See also
*
Bupivacaine
Bupivacaine, marketed under the brand name Marcaine among others, is a medication used to decrease sensation in a specific small area. In nerve blocks, it is injected around a nerve that supplies the area, or into the spinal canal's epidural ...
*
Efrapeptin
Efrapeptins are peptides produced by fungi in the genus '' Tolypocladium'' that have antifungal, insecticidal, and mitochondrial ATPase inhibitory activities. They are produced via a biosynthetic pathway similar to, but simpler than, the ciclospori ...
References
{{biochem-stub
Alpha-Amino acids
2-Piperidinyl compounds
Secondary amino acids