5-oxo-L-proline (CHEBI:18183)

ChEBI > Main

Main

ChEBI Ontology

Automatic Xrefs

Reactions

Pathways

Models

ChEBI Name	5-oxo-L-proline

ChEBI ID	CHEBI:18183

ChEBI ASCII Name	5-oxo-L-proline

Definition	An optically active form of 5-oxoproline having L-configuration.

Stars	This entity has been manually annotated by the ChEBI Team.

Secondary ChEBI IDs	CHEBI:44704, CHEBI:2113, CHEBI:12153, CHEBI:20619

Supplier Information	ZINC000008551531

Download	Molfile XML SDF

more structures >>

Wikipedia	License
Glycylglycine is the dipeptide of glycine, making it the simplest peptide. The compound was first synthesized by Emil Fischer and Ernest Fourneau in 1901 by boiling 2,5-diketopiperazine (glycine anhydride) with hydrochloric acid. Shaking with alkali and other synthesis methods have been reported. Because of its low toxicity, it is useful as a buffer for biological systems with effective ranges between pH 2.5–3.8 and 7.5–8.9; however, it is only moderately stable for storage once dissolved. It is used in the synthesis of more complex peptides. Glycylglycine has also been reported to be helpful in solubilizing recombinant proteins in E. coli. Using different concentrations of the glycylglycine improvement in protein solubility after cell lysis has been observed.
Read full article at Wikipedia

Formula

C5H7NO3

Net Charge

Average Mass

129.11400

Monoisotopic Mass

129.04259

InChI

InChI=1S/C5H7NO3/c7-4-2-1-3(6-4)5(8)9/h3H,1-2H2,(H,6,7)(H,8,9)/t3-/m0/s1

InChIKey

ODHCTXKNWHHXJC-VKHMYHEASA-N

SMILES

OC(=O)[C@@H]1CCC(=O)N1

Metabolite of Species	Details
Chlamydomonas reinhardtii (NCBI:txid3055)	See: PubMed

Roles Classification
Chemical Role(s):	Bronsted base A molecular entity capable of accepting a hydron from a donor (Bronsted acid). (via organic amino compound ) Bronsted acid A molecular entity capable of donating a hydron to an acceptor (Bronsted base). (via oxoacid )

Biological Role(s):	algal metabolite Any eukaryotic metabolite produced during a metabolic reaction in algae including unicellular organisms like chlorella and diatoms to multicellular organisms like giant kelps and brown algae. human metabolite Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens). (via 5-oxoproline )

ChEBI Ontology
Outgoing	5-oxo-L-proline (CHEBI:18183) has role algal metabolite (CHEBI:84735) 5-oxo-L-proline (CHEBI:18183) is a 5-oxoproline (CHEBI:16010) 5-oxo-L-proline (CHEBI:18183) is a L-proline derivative (CHEBI:84186) 5-oxo-L-proline (CHEBI:18183) is a non-proteinogenic L-α-amino acid (CHEBI:83822) 5-oxo-L-proline (CHEBI:18183) is conjugate acid of 5-oxo-L-prolinate (CHEBI:58402) 5-oxo-L-proline (CHEBI:18183) is enantiomer of 5-oxo-D-proline (CHEBI:16924)

Incoming	pyroglutamylglycine (CHEBI:83067) has functional parent 5-oxo-L-proline (CHEBI:18183) pyroglutamylvaline (CHEBI:132991) has functional parent 5-oxo-L-proline (CHEBI:18183) 5-oxo-L-prolinate (CHEBI:58402) is conjugate base of 5-oxo-L-proline (CHEBI:18183) 5-oxo-D-proline (CHEBI:16924) is enantiomer of 5-oxo-L-proline (CHEBI:18183) 5-oxo-L-proline residue (CHEBI:30652) is substituent group from 5-oxo-L-proline (CHEBI:18183) N-terminal 5-oxo-L-proline residue (CHEBI:87215) is substituent group from 5-oxo-L-proline (CHEBI:18183)

IUPAC Names

(2S)-5-oxopyrrolidine-2-carboxylic acid

5-oxo-L-proline

Synonyms	Sources
(−)-2-pyrrolidone-5-carboxylic acid	ChemIDplus
(S)-(−)-2-pyrrolidone-5-carboxylic acid	NIST Chemistry WebBook
(S)-pyroglutamic acid	ChemIDplus
5-Oxo-L-proline	KEGG COMPOUND
5-Oxo-L-proline	KEGG COMPOUND
5-Pyrrolidone-2-carboxylic acid	KEGG COMPOUND
L-5-Pyrrolidone-2-carboxylic acid	KEGG COMPOUND
L-Pyroglutamic acid	KEGG COMPOUND
pidolic acid	ChemIDplus
Pyroglutamate	KEGG COMPOUND
Pyroglutamic acid	KEGG COMPOUND
PYROGLUTAMIC ACID	PDBeChem

Citations

Last Modified

11 August 2016