1-Pyrroline-5-carboxylic acid

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

  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. ^ Heacock, Anne M.; Williams, Irene H.; Frank, Leonard H.; Adams, Elijah (1975-04-01). "Δ1-Pyrroline-5-carboxylate and Δ1-pyrroline-3-hydroxy-5-carboxylate: Chromatography on the amino acid analyzer". Analytical Biochemistry. 64 (2): 593–600. doi:10.1016/0003-2697(75)90472-8. ISSN 0003-2697. PMID 236687.