|Preferred IUPAC name
3D model (JSmol)
|Molar mass||113.115 g/mol|
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
|what is ?)(|
1-Pyrroline-5-carboxylic acid (systematic name 3,4-dihydro-2H-pyrrole-2-carboxylic acid) is a cyclic imino acid. Its conjugate base and anion is 1-pyrroline-5-carboxylate (P5C). In solution, P5C is in spontaneous equilibrium with glutamate-5-semialdhyde (GSA). 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.
In prokaryotic proline biosynthesis, GSA is synthesized from γ-glutamyl phosphate by the enzyme γ-glutamyl phosphate reductase. In most eukaryotes, GSA is synthesised from the amino acid glutamate by the bifunctional enzyme 1-pyrroline-5-carboxylate synthase (P5CS). The human P5CS is encoded by the ALDH18A1 gene. The enzyme pyrroline-5-carboxylate reductase converts P5C into proline
In proline degradation, the enzyme proline dehydrogenase produces P5C from proline, and the enzyme 1-pyrroline-5-carboxylate dehydrogenase converts GSA to glutamate. In many prokaryotes, proline dehydrogenase and P5C dehydrogenase form a bifunctional enzyme that prevents the release of P5C during proline degradation. In arginine degradation, the enzyme ornithine-δ-aminotransferase mediates the transamination between ornithine and a 2-oxo acid (typically 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.
- "computed by Chemicalize from ChemAxon". https://chemicalize.com/app/calculation/pyrroline-5-carboxylate.
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- "Assignment of the human gene encoding the delta 1-pyrroline-5-carboxylate synthetase (P5CS) to 10q24.3 by in situ hybridization". Genomics 37 (1): 145–6. Oct 1996. doi:10.1006/geno.1996.0535. PMID 8921385.
- "Entrez Gene: ALDH18A1 aldehyde dehydrogenase 18 family, member A1". https://www.ncbi.nlm.nih.gov/sites/entrez?Db=gene&Cmd=ShowDetailView&TermToSearch=5832.
- Liu, Li-Kai; Becker, Donald F.; Tanner, John J. (2017-10-15). "Structure, function, and mechanism of proline utilization A (PutA)" (in en). Archives of Biochemistry and Biophysics. Flavoproteins: Beyond the Classical Paradigms 632: 142–157. doi:10.1016/j.abb.2017.07.005. ISSN 0003-9861. PMID 28712849.
Original source: https://en.wikipedia.org/wiki/1-Pyrroline-5-carboxylic acid. Read more