γ-Glu-Phe

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.

Product information

CAS Number: 7432-24-8

Molecular Weight: 294.30

Formula: C14H18N2O5

Synonym:

γ-Glutamylphenylalanine

Chemical Name: (S)-2-amino-5-((S)-1-carboxy-2-phenylethylamino)-5-oxopentanoic acid

Smiles: N[C@@H](CCC(=O)N[C@@H](CC1C=CC=CC=1)C(O)=O)C(O)=O

InChiKey: XHHOHZPNYFQJKL-QWRGUYRKSA-N

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

Technical Data

Appearance: Solid Power

Purity: ≥98% (or refer to the Certificate of Analysis)

Solubility: H2O : ≥ 50 mg/mL (169.89 mM).

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical or refer to Certificate of Analysis

Storage Condition: Dry, dark and -20 ^oC for 1 year or refer to the Certificate of Analysis.

Shelf Life: ≥12 months if stored properly.

Stock Solution Storage: 0 - 4 ^oC for 1 month or refer to the Certificate of Analysis.

Drug Formulation: To be determined

HS Tariff Code: 382200

How to use

In Vitro:

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.

References:

1. 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.
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.

Products are for research use only. Not for human use.