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4-(γ-Glutamylamino)butanoic acid

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4-(γ-Glutamylamino)butanoic acid
Stereo, skeletal formula of 4-(γ-glutamylamino)butanoic acid (S)
Names
Preferred IUPAC name 2-Amino-5--5-oxopentanoic acid
Systematic IUPAC name 4-Amino-5-((3-carboxypropyl)amino)-5-oxopentanoic acid
Other names
  • 2-Amino-5-(3-carboxypropylamino)-5-oxopentanoic acid
  • 4-(Glutam-5-ylamino)butanoic acid
  • γ-Glutamyl-γ-aminobutyric acid
Identifiers
CAS Number
3D model (JSmol)
Abbreviations
  • Glutamyl-GABA
  • Glu-GABA
  • γ-Glutamyl-GABA
  • γ-Glu-γ-Abu
Beilstein Reference 2418119
ChEBI
ChEMBL
ChemSpider
KEGG
PubChem CID
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C9H16N2O5/c10-6(9(15)16)3-4-7(12)11-5-1-2-8(13)14/h6H,1-5,10H2,(H,11,12)(H,13,14)(H,15,16)Key: MKYPKZSGLSOGLL-UHFFFAOYSA-N
SMILES
  • NC(CCC(=O)NCCCC(O)=O)C(O)=O
Properties
Chemical formula C9H16N2O5
Molar mass 232.236 g·mol
log P −1.434
Acidity (pKa) 2.223
Basicity (pKb) 11.777
Related compounds
Related alkanoic acids
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

4-(γ-Glutamylamino)butanoic acid is molecule that consists of L-glutamate conjugated to γ-aminobutyric acid (GABA). It is the substrate of the enzyme γ-glutamyl-γ-aminobutyrate hydrolase, which is involved in the biosynthesis of polyamines.

References

  1. "NSC609423 - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 26 March 2005. Identification. Retrieved 8 July 2012.
  2. Kurihara S, Oda S, Kato K, Kim HG, Koyanagi T, Kumagai H, Suzuki H (2005). "A novel putrescine utilization pathway involves gamma-glutamylated intermediates of Escherichia coli K-12". J. Biol. Chem. 280 (6): 4602–8. doi:10.1074/jbc.M411114200. PMID 15590624.


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