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

CAS Number

* 2906-39-0 N

3D model (JSmol)

* Interactive image
* Interactive image

ChEBI |

* CHEBI:1372 Y

ChEMBL |

* ChEMBL1161508 Y

ChemSpider |

* 1159 Y

KEGG |

* C04322 Y

MeSH | Delta-1-pyrroline-5-carboxylate

PubChem CID

* 1196

UNII |

* 52TNU46DHL Y

InChI

* InChI=1S/C5H7NO2/c7-5(8)4-2-1-3-6-4/h3-4H,1-2H2,(H,7,8) Y

Key: DWAKNKKXGALPNW-UHFFFAOYSA-N Y

* InChI=1/C5H7NO2/c7-5(8)4-2-1-3-6-4/h3-4H,1-2H2,(H,7,8)

Key: DWAKNKKXGALPNW-UHFFFAOYAB

SMILES

* C1CC(N=C1)C(=O)O

* O=C(O)C1/N=C\CC1

Properties

Chemical formula

| 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 YN ?)
Infobox references

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-semialdehyde (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 prokaryotic proline biosynthesis, GSA is synthesized from γ-glutamyl phosphate by the enzyme γ-glutamyl phosphate reductase.[7]

Template:Chemrxn

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.[8][9] The enzyme pyrroline-5-carboxylate reductase converts L-P5C into proline.[10]

Template:Chemrxn

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.[11]

A reciprocal regulation of delta 1-pyrroline-5-carboxylate synthetase (P5CS) and proline dehydrogenase genes controls proline levels during and after osmotic stress in plants proportional to the level of proline.[12] This allows an optimum level of proline to be produced from reduced nitrogen to control osmotic stress.

## References

1. ↑ "computed by Chemicalize from ChemAxon". https://chemicalize.com/app/calculation/pyrroline-5-carboxylate.
2. ↑ PubChem. "3,4-Dihydro-2H-pyrrole-2-carboxylic acid" (in en). https://pubchem.ncbi.nlm.nih.gov/compound/1196.
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" (in en). Analytical Biochemistry 64 (2): 593–600. doi:10.1016/0003-2697(75)90472-8. ISSN 0003-2697. PMID 236687.
4. ↑ Bertolo, Robert F.; Burrin, Douglas G. (2008-10-01). "Comparative Aspects of Tissue Glutamine and Proline Metabolism" (in en). The Journal of Nutrition 138 (10): 2032S–2039S. doi:10.1093/jn/138.10.2032S. ISSN 0022-3166. PMID 18806120.
5. ↑ Qamar, Aarzoo; Mysore, Kirankumar; Senthil-Kumar, Muthappa (2015). "Role of proline and pyrroline-5-carboxylate metabolism in plant defense against invading pathogens" (in en). Frontiers in Plant Science 6: 503. doi:10.3389/fpls.2015.00503. ISSN 1664-462X. PMID 26217357. Bibcode: 2015FrPS....6..503Q.
6. ↑ Winter, Gudrun; Todd, Christopher D.; Trovato, Maurizio; Forlani, Giuseppe; Funck, Dietmar (2015). "Physiological implications of arginine metabolism in plants" (in en). Frontiers in Plant Science 6: 534. doi:10.3389/fpls.2015.00534. ISSN 1664-462X. PMID 26284079. Bibcode: 2015FrPS....6..534W.
7. ↑ "The biosynthesis of proline in Escherichia coli: phosphate-dependent glutamate -semialdehyde dehydrogenase (NADP), the second enzyme in the pathway". Biochimica et Biophysica Acta 244 (1): 129–34. July 1971. doi:10.1016/0304-4165(71)90129-2. PMID 4399189.
8. ↑ "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.
9. ↑ "Entrez Gene: ALDH18A1 aldehyde dehydrogenase 18 family, member A1". https://www.ncbi.nlm.nih.gov/gene?Db=gene&Cmd=ShowDetailView&TermToSearch=5832.
10. ↑ Smith ME; Greenberg DM (1956). "Characterization of an enzyme reducing pyrroline-5-carboxylate to proline". Nature 177 (4520): 1130. doi:10.1038/1771130a0. PMID 13334497. Bibcode: 1956Natur.177.1130S.
11. ↑ 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.
12. ↑ Verma, D.P.S (December 1996). "Reciprocal regulation of delta 1-pyrroline-5-carboxylate synthetase and proline dehydrogenase genes controls proline levels during and after osmotic stress in plants". Molecular Genetics 253 (3): 334–341. doi:10.1007/pl00008600. PMID 9003320.

* v
* t
* e

Amino acid metabolism metabolic intermediates

K→acetyl-CoA|

| lysine→|

* Saccharopine
* Allysine
* α-Aminoadipic acid
* α-Ketoadipate
* Glutaryl-CoA
* Glutaconyl-CoA
* Crotonyl-CoA
* β-Hydroxybutyryl-CoA

|

leucine→|

* β-Hydroxy β-methylbutyric acid
* β-Hydroxy β-methylbutyryl-CoA
* Isovaleryl-CoA
* α-Ketoisocaproic acid
* β-Ketoisocaproic acid
* β-Ketoisocaproyl-CoA
* β-Leucine
* β-Methylcrotonyl-CoA
* β-Methylglutaconyl-CoA
* β-Hydroxy β-methylglutaryl-CoA

tryptophan→alanine→|

* N'-Formylkynurenine
* Kynurenine
* Anthranilic acid
* 3-Hydroxykynurenine
* 3-Hydroxyanthranilic acid
* 2-Amino-3-carboxymuconic semialdehyde
* 2-Aminomuconic semialdehyde
* 2-Aminomuconic acid
* Glutaryl-CoA

| G→pyruvate→citrate|

| glycine→serine→|

* 3-Phosphoglyceric acid

* glycine→creatine: Glycocyamine
* Phosphocreatine
* Creatinine

|

G→glutamate→
α-ketoglutarate|

| histidine→|

* Urocanic acid
* Imidazol-4-one-5-propionic acid
* Formiminoglutamic acid
* Glutamate-1-semialdehyde

|

proline→|

* 1-Pyrroline-5-carboxylic acid

arginine→|

* Agmatine
* Ornithine
* Citrulline
* Cadaverine
* Putrescine

other|

* cysteine+glutamate→glutathione: γ-Glutamylcysteine

G→propionyl-CoA→
succinyl-CoA|

| valine→|

* α-Ketoisovaleric acid
* Isobutyryl-CoA
* Methacrylyl-CoA
* 3-Hydroxyisobutyryl-CoA
* 3-Hydroxyisobutyric acid
* 2-Methyl-3-oxopropanoic acid

|

isoleucine→|

* 2,3-Dihydroxy-3-methylpentanoic acid
* 2-Methylbutyryl-CoA
* Tiglyl-CoA
* 2-Methylacetoacetyl-CoA

methionine→|

* generation of homocysteine: S-Adenosyl methionine
* S-Adenosyl-L-homocysteine
* Homocysteine

* conversion to cysteine: Cystathionine
* α-Ketobutyric acid+Cysteine

threonine→|

* α-Ketobutyric acid

propionyl-CoA→|

* Methylmalonyl-CoA

G→fumarate|

| [[Chemistry:Phenylphenylalanine]]→tyrosine→|

* 4-Hydroxyphenylpyruvic acid
* Homogentisic acid
* 4-Maleylacetoacetic acid

|

G→oxaloacetate|

* see urea cycle

Other|

| Cysteine metabolism|

* Cysteine sulfinic acid

|

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