1-Pyrroline-5-carboxylic acid
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Names | |
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Preferred IUPAC name
3,4-Dihydro-2H-pyrrole-2-carboxylic acid | |
Other names
1-Pyrroline-5-carboxylic acid
δ-1-Pyrroline-5-carboxylic acid P5C | |
Identifiers | |
3D model (
JSmol ) |
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ChEBI | |
ChEMBL | |
ChemSpider | |
KEGG | |
MeSH | Delta-1-pyrroline-5-carboxylate |
PubChem CID
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UNII | |
CompTox Dashboard (EPA)
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Properties | |
C5H7NO2 | |
Molar mass | 113.115 g/mol |
Acidity (pKa) | 1.82/6.07[1] |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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1-Pyrroline-5-carboxylic acid (systematic name 3,4-dihydro-2H-pyrrole-2-carboxylic acidanion is 1-pyrroline-5-carboxylate (P5C). In solution, P5C is in spontaneous equilibrium with glutamate-5-semialdhyde (GSA).[3]
Biochemistry
The
stereoisomer (S)-1-pyrroline-5-carboxylate (also referred to as L-P5C) is an intermediate metabolite in the biosynthesis and degradation of proline and arginine.[4][5][6]
In
glutamate by the bifunctional enzyme 1-pyrroline-5-carboxylate synthase (P5CS). The human P5CS is encoded by the ALDH18A1 gene.[7][8] The enzyme pyrroline-5-carboxylate reductase
converts P5C into proline
In proline degradation, the enzyme
α-ketoglutarate) to form P5C and an L-amino acid (typically glutamate). Under specific conditions, P5C may also be used for arginine biosynthesis via the reverse reaction of ornithine-δ-aminotransferase.[4]
References
- ^ "computed by Chemicalize from ChemAxon".
- ^ PubChem. "3,4-Dihydro-2H-pyrrole-2-carboxylic acid". pubchem.ncbi.nlm.nih.gov. Retrieved 2020-01-23.
- PMID 236687.
- ^ PMID 18806120.
- PMID 26217357.
- PMID 26284079.
- PMID 8921385.
- ^ "Entrez Gene: ALDH18A1 aldehyde dehydrogenase 18 family, member A1".
- PMID 28712849.