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MetaCyc Compound: (S)-1-pyrroline-5-carboxylate

Synonyms: pyrroline 5-carboxylate, L-Δ1-pyrroline-5-carboxylate, 1-pyrroline-5-carboxylate, L-1-pyrroline-5-carboxylate, δ-1-pyrroline-5-carboxylic acid, δ-1-pyrroline-5-carboxylate

Superclasses: an acid all carboxy acids a carboxylate a monocarboxylate 1-pyrroline-5-carboxylate
an organic heterocyclic compound an organic heteromonocyclic compound a pyrroline 1-pyrroline-5-carboxylate
an organic heterocyclic compound an organonitrogen heterocyclic compound a pyrroline 1-pyrroline-5-carboxylate

Summary:
(S)-1-pyrroline-5-carboxylate is an enamine that forms on spontaneous dehydration of L-glutamate-5-semialdehyde in aqueous solutions. It can be converted to or be formed from the three amino acids L-glutamate (EC 1.2.1.88, L-glutamate γ-semialdehyde dehydrogenase), L-ornithine (EC 2.6.1.13, ornithine aminotransferase) and L-proline (EC 1.5.99.8, proline dehydrogenase and EC 1.5.1.2, pyrroline-5-carboxylate reductase). It is also one of the few metabolites that can be a precursor to other metabolites of both the urea cycle and the TCA cycle I (prokaryotic).

Chemical Formula: C5H6NO2

Molecular Weight: 112.11 Daltons

Monoisotopic Molecular Weight: 113.0476784741 Daltons

(<i>S</i>)-1-pyrroline-5-carboxylate compound structure

SMILES: C1(=NC(CC1)C(=O)[O-])

InChI: InChI=1S/C5H7NO2/c7-5(8)4-2-1-3-6-4/h3-4H,1-2H2,(H,7,8)/p-1/t4-/m0/s1

InChIKey: InChIKey=DWAKNKKXGALPNW-BYPYZUCNSA-M

Unification Links: CAS:2906-39-0 , ChEBI:17388 , ChemSpider:10140174 , HMDB:HMDB01301 , IAF1260:42766 , KEGG:C03912 , MetaboLights:MTBLC17388 , PubChem:11966181

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): -3.4353373 Inferred by computational analysis [Latendresse13]

Reactions known to consume the compound:

(5R)-carbapenem carboxylate biosynthesis :
(S)-1-pyrroline-5-carboxylate + malonyl-CoA + H+ + H2O → (2S,5S)-5-carboxymethyl proline + CO2 + coenzyme A

L-arginine degradation VI (arginase 2 pathway) , L-ornithine degradation II (Stickland reaction) , L-proline biosynthesis I , L-proline biosynthesis II (from arginine) , L-proline biosynthesis III :
L-proline + NAD(P)+(S)-1-pyrroline-5-carboxylate + NAD(P)H + 2 H+

peramine biosynthesis :
(S)-1-pyrroline-5-carboxylate + L-arginine + S-adenosyl-L-methionine + 2 ATP → peramine + S-adenosyl-L-homocysteine + 2 AMP + 2 diphosphate + H2O + 2 H+

Not in pathways:
(S)-1-pyrroline-5-carboxylate + NAD+ + 2 H2O → L-glutamate + NADH + H+

methyl ketone biosynthesis :
a carboxylate + ATP + coenzyme A → an acyl-CoA + AMP + diphosphate

Not in pathways:
an acyl-protein synthetase + a carboxylate + ATP → an acyl-protein thioester + AMP + diphosphate
a carboxylate + GTP + coenzyme A → an acyl-CoA + GDP + phosphate

Reactions known to produce the compound:

(5R)-carbapenem carboxylate biosynthesis , L-citrulline biosynthesis , L-Nδ-acetylornithine biosynthesis , L-proline degradation :
L-proline + an electron-transfer quinone[inner membrane](S)-1-pyrroline-5-carboxylate + an electron-transfer quinol[inner membrane] + H+

ethylene biosynthesis II (microbes) :
(3S)-3-hydroxy-L-arginine → guanidinium + (S)-1-pyrroline-5-carboxylate + H+ + H2O

ethylene biosynthesis IV :
2-oxoglutarate + L-arginine + oxygen → succinate + CO2 + guanidinium + (S)-1-pyrroline-5-carboxylate + H2O + H+

proline to cytochrome bo oxidase electron transfer :
L-proline + an ubiquinone[inner membrane](S)-1-pyrroline-5-carboxylate + an ubiquinol[inner membrane] + H+

Not in pathways:
3 2-oxoglutarate + L-arginine + 3 oxygen + 3 H+ → 2 ethylene + 7 CO2 + succinate + guanidinium + (S)-1-pyrroline-5-carboxylate + 3 H2O
L-proline[in] + an ubiquinone[in](S)-1-pyrroline-5-carboxylate[in] + an ubiquinol[in] + H+[in]

3,3'-thiodipropanoate degradation :
3-sulfinopropionate + an acyl-CoA → 3-sulfinopropanoyl-CoA + a carboxylate

dimethylsulfoniopropanoate degradation II (cleavage) :
dimethylsulfoniopropanoate + an acyl-CoA → dimethylsulfoniopropioyl-CoA + a carboxylate

NAD/NADP-NADH/NADPH mitochondrial interconversion (yeast) :
an aldehyde + NADP+ + H2O → a carboxylate + NADPH + 2 H+
an aldehyde + NAD+ + H2O → a carboxylate + NADH + 2 H+

phosphatidylcholine resynthesis via glycerophosphocholine :
a phosphatidylcholine + 2 H2O → sn-glycero-3-phosphocholine + 2 a carboxylate + 2 H+

Not in pathways:
a 1-acyl 2-lyso-phosphatidylcholine[periplasmic space] + H2O[periplasmic space]a carboxylate[periplasmic space] + sn-glycero-3-phosphocholine[periplasmic space] + H+[periplasmic space]
an acyl-CoA + H2O → a carboxylate + coenzyme A + H+
an L-1-phosphatidyl-inositol + H2O → a 1-acyl-sn-glycero-3-phospho-D-myo-inositol + a carboxylate + H+
a carboxylic ester + H2O → an alcohol + a carboxylate + H+
an aldehyde + oxygen + H2O → a carboxylate + hydrogen peroxide + H+
an aldehyde + FMNH2 + oxygen → hν + a carboxylate + FMN + H2O + 2 H+
an acylcholine + H2O → choline + a carboxylate + H+
a 1,2-diacyl-3-β-D-galactosyl-sn-glycerol + 2 H2O → 2 a carboxylate + 3-β-D-galactosyl-sn-glycerol + 2 H+
an acyl phosphate + H2O → a carboxylate + phosphate + H+
an S-acylglutathione + H2O → a carboxylate + glutathione
an N-acyl-L-aspartate + H2O → L-aspartate + a carboxylate

Reactions known to both consume and produce the compound:

ethylene biosynthesis II (microbes) , L-arginine degradation VI (arginase 2 pathway) , L-citrulline biosynthesis , L-Nδ-acetylornithine biosynthesis , L-ornithine degradation II (Stickland reaction) , L-proline biosynthesis I , L-proline biosynthesis II (from arginine) , L-proline biosynthesis III , L-proline degradation :
(S)-1-pyrroline-5-carboxylate + H+ + H2O ↔ L-glutamate-5-semialdehyde

Not in pathways:
L-ornithine + 2-oxoglutarate ↔ 1-pyrroline-5-carboxylate + L-glutamate + H+ + H2O

sphingolipid recycling and degradation (yeast) :
a dihydroceramide + H2O ↔ sphinganine + a carboxylate

In Reactions of unknown directionality:

Not in pathways:
(S)-1-pyrroline-5-carboxylate + NAD(P)+ + 2 H2O = L-glutamate + NAD(P)H + H+

Not in pathways:
a monocarboxylic-acid-amide + H2O = a monocarboxylate + ammonium

Not in pathways:
eugenol + a carboxylate + NADP+ = a coniferyl ester + NADPH
a 2-acyl 1-lyso-phosphatidylcholine[periplasmic space] + H2O[periplasmic space] = a carboxylate[periplasmic space] + sn-glycero-3-phosphocholine[periplasmic space] + H+[periplasmic space]
an aldehyde + an electron-transfer quinone + H2O = a carboxylate + an electron-transfer quinol + H+
a triacyl-sn-glycerol + H2O = a 1,2-diacyl-sn-glycerol + a carboxylate + H+
a penicillin + H2O = 6-aminopenicillanate + a carboxylate
an aldehyde[periplasmic space] + FAD[periplasmic space] + H2O[periplasmic space] = a carboxylate[periplasmic space] + FADH2[periplasmic space]
a nitrile + 2 H2O = a carboxylate + ammonium
an aliphatic nitrile + 2 H2O = a carboxylate + ammonium
an N-acyl-L-homoserine lactone + H2O = L-homoserine lactone + a carboxylate
an aldehyde + an unknown oxidized electron acceptor + H2O = a carboxylate + an unknown reduced electron acceptor + H+
an N-acylated aromatic-L-amino acid + H2O = a carboxylate + an aromatic L-amino acid
an N-acylated-D-amino acid + H2O = a D-amino acid + a carboxylate
an N-acylated aliphatic-L-amino acid + H2O = a carboxylate + an aliphatic L-amino acid
a D-hexose + an acyl phosphate = a D-hexose-phosphate + a carboxylate
an aldehyde + 2 an oxidized ferredoxin + H2O = a carboxylate + 2 a reduced ferredoxin + 3 H+
an aldehyde + NAD(P)+ + H2O = a carboxylate + NAD(P)H + 2 H+
an N-acyl-D-glutamate + H2O = a carboxylate + D-glutamate
an anilide + H2O = aniline + a carboxylate + H+
a 5'-acylphosphoadenosine + H2O = a carboxylate + AMP + 2 H+
a 3-acylpyruvate + H2O = a carboxylate + pyruvate + H+
an N6acyl-L-lysine + H2O = a carboxylate + L-lysine
an N-acyl-D-aspartate + H2O = a carboxylate + D-aspartate

In Redox half-reactions:
(S)-1-pyrroline-5-carboxylate[in] + 3 H+[in] + 2 e-[membrane] → L-proline[in]

This compound has been characterized as an alternative substrate of the following enzymes: Δ1-pyrroline-3-hydroxy-5-carboxylate dehydrogenase

Credits:
Revised 16-Jul-2013 by Caspi R , SRI International


References

Latendresse13: Latendresse M. (2013). "Computing Gibbs Free Energy of Compounds and Reactions in MetaCyc."


Report Errors or Provide Feedback
Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
Page generated by SRI International Pathway Tools version 19.0 on Sat Apr 18, 2015, BIOCYC13B.