gamma-glutamylalanine

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  • Name: gamma-glutamylalanine
  • Description: gamma-Glutamylalanine is a dipeptide composed of gamma-glutamate and alanine, and is a proteolytic breakdown product of larger proteins. It belongs to the family of N-acyl-alpha amino acids and der... ivatives. These are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom. gamma-Glutamylalanine is a natural substrate of the enzyme (5-L-glutamyl)-L-amino acid 5-glutamyltransferase (cyclizing) (g-glutamylcyclotransferase, EC 2. 3. 2. 2) in the glutathione metabolism pathway, which cleaves gamma-glutamylalanine to produce L-5-oxoproline. gamma-Glutamylcyclotransferase is widely distributed in both human and animal tissues where it catalyzes the scission of the y-peptide bonds of many different gamma-glutamyl-amino acids and gamma-glutamyl-gamma-glutamyl-amino acids. The latter are 'better' substrates of the enzyme than the corresponding gamma-glutamyl-amino acids (PMID: 2570694, 2893631).
Overview of age-variations
Age group comparisons
PMID Age/Age interval, Gender Value (unit of measurement) Method Sample
27374292 Age [25–35] (median=32), Gender ♀ (Japanese) 0.825714 (average level of metabolite) UHPLC-MS/MS Positive mode serum
27374292 Age [55–65] (median=60), Gender ♀ (Japanese) 1.014241 (average level of metabolite) UHPLC-MS/MS Positive mode serum
Linear regression
PMID Age/Age interval, Gender Value (unit of measurement) Method Sample
log2 ratio/log2(FC)
PMID Age/Age interval, Gender Value (unit of measurement) Method Sample
Summary
  • Synonym:
    γ-L-glutamyl-L-alanine; gamma-L-glutamyl-L-alanine; γ-Glu-Ala; gamma-Glu-Ala; (2S)-2-amino-5-[[(1S)-1-carboxyethyl]amino]-5-oxovaleric acid;gamma-L-glutamyl-L-alanine
  • Chemical Formula:
    C8H14N2O5
  • Systematic name:
    (2S)-2-amino-5-[[(1S)-1-carboxyethyl]amino]-5-oxopentanoic acid
  • SMILES:
    CC(C(=O)O)NC(=O)CCC(C(=O)O)N
  • InChI:
    InChI=1S/C8H14N2O5/c1-4(7(12)13)10-6(11)3-2-5(9)8(14)15/h4-5H,2-3,9H2,1H3,(H,10,11)(H,12,13)(H,14,15)/t4-,5-/m0/s1
  • InChI Key:
    WQXXXVRAFAKQJM-WHFBIAKZSA-N
  • CAS number:
    5875-41-2
Related resources
Metabolite sources and localization
  • Metabolite location:
    Human organism, Body part, Extracellular, Human body biofluids, Biofluid tissues, Blood, Serum, Tissue
  • Metabolite source:
    Homo sapiens, endogenous metabolite
Age-variations
Age group comparisons
Method: UHPLC-MS/MS Positive mode
Sample: serum
PubMed PMID: 27374292
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