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MetaCyc Compound: D-proline

Superclasses: an amino acid or its derivative an amino acid a D-amino acid

Chemical Formula: C5H9NO2

Molecular Weight: 115.13 Daltons

Monoisotopic Molecular Weight: 115.0633285383 Daltons

D-proline compound structure

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

InChI: InChI=1S/C5H9NO2/c7-5(8)4-2-1-3-6-4/h4,6H,1-3H2,(H,7,8)/t4-/m1/s1

InChIKey: InChIKey=ONIBWKKTOPOVIA-SCSAIBSYSA-N

Unification Links: CAS:344-25-2 , ChEBI:57726 , HMDB:HMDB03411 , KEGG:C00763 , MetaboLights:MTBLC57726 , PubChem:6971012

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): 23.720093 Inferred by computational analysis [Latendresse13]

Reactions known to consume the compound:

Not in pathways:
a D-amino acid[in] + an electron-transfer quinone[membrane] + H2O[in] → a 2-oxo carboxylate[in] + ammonium[in] + an electron-transfer quinol[membrane]
a D-amino acid + oxygen + H2O → ammonium + hydrogen peroxide + a 2-oxo carboxylate

Reactions known to produce the compound:

Not in pathways:
a peptide with an N-terminal D-amino acid + H2O → a peptide + a D-amino acid + H+
a D-aminoacyl-[tRNA] + H2O → a D-amino acid + an uncharged tRNA + 2 H+

Reactions known to both consume and produce the compound:

L-ornithine degradation II (Stickland reaction) :
L-proline ↔ D-proline
D-proline + NADH + H+ ↔ 5-aminopentanoate + NAD+

Not in pathways:
5-aminopentanoate + (R)-lipoate ↔ dihydrolipoate + D-proline

In Reactions of unknown directionality:

Not in pathways:
D-proline + an ubiquinone = 1-pyrroline-2-carboxylate + an ubiquinol + H+
D-proline + an unknown oxidized electron acceptor = 1-pyrroline-2-carboxylate + an unknown reduced electron acceptor + H+

Not in pathways:
acetyl-CoA + a D-amino acid = an N-acetyl-D-amino acid + coenzyme A + H+
an N-carbamoyl D-amino acid + H+ + H2O = a D-amino acid + ammonium + CO2
an N-acylated-D-amino acid + H2O = a D-amino acid + a carboxylate
an L-amino acid = a D-amino acid

Not in pathways:
a 5-L-glutamyl-[peptide] + an amino acid = a 5-L-glutamyl-amino acid + a peptide

In Redox half-reactions:
a 2-oxo carboxylate[in] + ammonium[in] + 2 H+[in] + 2 e-[membrane]a D-amino acid[in] + H2O[in]

Enzymes inhibited by D-proline, sorted by the type of inhibition, are:

Inhibitor (Competitive) of: Δ1-pyrroline-3-hydroxy-5-carboxylate dehydrogenase [Adams60]

This compound has been characterized as an alternative substrate of the following enzymes: D-hydroxyproline dehydrogenase , cis-4-hydroxy-D-proline dehydrogenase


References

Adams60: Adams, E., Goldstone, A. (1960). "Hydroxyproline metabolism. IV. Enzymatic synthesis of gamma-hydroxyglutamate from Delta 1-pyrroline-3-hydroxy-5-carboxylate." J Biol Chem 235;3504-12. PMID: 13681370

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 Sun May 24, 2015, biocyc13.