γ-Glu-Phe

• CAT Number: M006497
• CAS Number: 7432-24-8
• Molecular Formula: C14H18N2O5
• Molecular Weight: 294.30
• Purity: ≥95%
• Synonyms: (2S)-2-amino-5-[[(1S)-1-carboxy-2-phenylethyl]amino]-5-oxopentanoic acid
• InChI: InChI=1S/C14H18N2O5/c15-10(13(18)19)6-7-12(17)16-11(14(20)21)8-9-4-2-1-3-5-9/h1-5,10-11H,6-8,15H2,(H,16,17)(H,18,19)(H,20,21)/t10-,11-/m0/s1
• InChIKey: XHHOHZPNYFQJKL-QWRGUYRKSA-N
• SMILES: C1=CC=C(C=C1)CC(C(=O)O)NC(=O)CCC(C(=O)O)N

γ-Glu-Phe (γ-Glutamylphenylalanine) is synthesized by Bacillus amyloliquefaciens (GBA) and Aspergillus oryzae (GAO). γ-Glu-Phe or the post-enzymatic reaction mixture enhances the umami intensity of commercial soy sauce and model chicken broth[1].
γ-Glu-Phe, γ-Glu-Met and γ-Glu-Val, are identified in sourdough by liquid chromatography-tandem mass spectrometry in MRM mode. γ-Glutamyl dipeptides are found in higher concentrations in sourdough fermented with L. reuteri when compared to the chemically acidified controls. Proteolysis is an important factor for generation of γ-glutamyl dipeptides. Sensory evaluation of bread reveals that sourdough bread with higher concentrations of γ-glutamyl dipeptides ranks higher with respect to the taste intensity when compared to regular bread and type I sourdough bread. Sourdough breads fermented with L. reuteri LTH5448 and L. reuteri 100-23 differ with respect to the intensity of the salty taste; this difference corresponds to a different concentration of γ-glutamyl dipeptides[2].

Reference

[1]. Zhao CJ, et al. Synthesis of Taste-Active γ-Glutamyl Dipeptides during Sourdough Fermentation by Lactobacillus reuteri. J Agric Food Chem. 2016 Oct 12;64(40):7561-7568.
 [Content Brief]

[2]. Zhao CJ, et al. Synthesis of Taste-Active γ-Glutamyl Dipeptides during Sourdough Fermentation by Lactobacillus reuteri. J Agric Food Chem. 2016 Oct 12;64(40):7561-7568.

[3]. Yang J, et al. Synthesis and Sensory Characteristics of Kokumi γ-[Glu]n-Phe in the Presence of Glutamine and Phenylalanine: Glutaminase from Bacillus amyloliquefaciens or Aspergillus oryzae as the Catalyst. J Agric Food Chem. 2017 Oct 4;65(39):8696-8703.
 [Content Brief]