γ-Glu-Phe peptide

γ-Glu-Phe peptide

• Handling and Storage of Synthetic Peptides
• Material Safety Data Sheets (MSDS)

Batch to batch variation of the purity

γ-EF

H-γGlu-Phe-OH

2

95.9%

C₁₄H₁₈N₂O₅

294.3

7432-24-8

111299

Synthetic

Powder

γ-Glu-Phe, or gamma-glutamyl-phenylalanine, is a dipeptide consisting of two amino acids, glutamic acid (Glu) and phenylalanine (Phe). In this peptide, the carboxyl group of the glutamic acid forms a peptide bond with the amino group of the phenylalanine. γ-Glu-Phe is known for its savory, or umami, taste. It contributes to the overall flavor of certain foods, enhancing their taste without adding additional salt. This dipeptide can be found in various fermented foods, such as cheese and soy sauce, where it is formed through microbial activity and enzymatic reactions during the fermentation process. The presence of γ-Glu-Phe and other γ-glutamyl dipeptides in foods can contribute to a more complex and satisfying taste experience, which is particularly important in low-salt or reduced-fat food products where the perception of saltiness or richness may be diminished.

Normally, this peptide will be delivered in lyophilized form and should be stored in a freezer at or below -20 °C. For more details, please refer to the manual: Handling and Storage of Synthetic Peptides

• Zhao CJ, Gänzle MG. Synthesis of Taste-Active γ-Glutamyl Dipeptides during Sourdough Fermentation by Lactobacillus reuteri. J Agric Food Chem. 2016 Oct 12;64(40):7561-7568. doi: 10.1021/acs.jafc.6b02298. Epub 2016 Sep 29. PMID: 27641253.

Trifluoroacetic acid (TFA) has a significant impact on peptides due to its role in the peptide synthesis process.

TFA is essential for the protonation of peptides that lack basic amino acids such as Arginine (Arg), Histidine (His), and Lysine (Lys), or ones that have blocked N-termini. As a result, peptides often contain TFA salts in the final product.

TFA residues, when present in custom peptides, can cause unpredictable fluctuations in experimental data. At a nanomolar (nM) level, TFA can influence cell experiments, hindering cell growth at low concentrations (as low as 10 nM) and promoting it at higher doses (0.5–7.0 mM). It can also serve as an allosteric regulator on the GlyR of glycine receptors, thereby increasing receptor activity at lower glycine concentrations.

In an in vivo setting, TFA can trifluoroacetylate amino groups in proteins and phospholipids, inducing potentially unwanted antibody responses. Moreover, TFA can impact structure studies as it affects spectrum absorption.