1-Pyrroline-5-carboxylic acid

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1-Pyrroline-5-carboxylic acid
Names
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
)
ChEBI
ChEMBL
ChemSpider
KEGG
MeSH Delta-1-pyrroline-5-carboxylate
UNII
  • InChI=1S/C5H7NO2/c7-5(8)4-2-1-3-6-4/h3-4H,1-2H2,(H,7,8) checkY
    Key: DWAKNKKXGALPNW-UHFFFAOYSA-N checkY
  • InChI=1/C5H7NO2/c7-5(8)4-2-1-3-6-4/h3-4H,1-2H2,(H,7,8)
    Key: DWAKNKKXGALPNW-UHFFFAOYAB
  • C1CC(N=C1)C(=O)O
  • O=C(O)C1/N=C\CC1
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).
☒N verify (what is checkY☒N ?)

1-Pyrroline-5-carboxylic acid (systematic name 3,4-dihydro-2H-pyrrole-2-carboxylic acid

anion 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

  1. ^ "computed by Chemicalize from ChemAxon".
  2. ^ PubChem. "3,4-Dihydro-2H-pyrrole-2-carboxylic acid". pubchem.ncbi.nlm.nih.gov. Retrieved 2020-01-23.
  3. PMID 236687
    .
  4. ^ .
  5. .
  6. .
  7. .
  8. ^ "Entrez Gene: ALDH18A1 aldehyde dehydrogenase 18 family, member A1".
  9. PMID 28712849
    .