γ-Glu-Phe TFA (γ-Glutamylphenylalanine TFA) is synthesized by Bacillus amyloliquefaciens (GBA) and Aspergillus oryzae (GAO). γ-Glu-Phe TFA or post-enzyme reaction mixture enhances the umami intensity of commercial soy sauce and model chicken stock.

Physicochemical Properties

Molecular Formula	C16H19F3N2O7
Molecular Weight	408.33
Exact Mass	408.114
CAS #	2828432-42-2
Related CAS #	γ-Glu-Phe;7432-24-8
PubChem CID	146014420
Appearance	White to off-white solid powder
Hydrogen Bond Donor Count	5
Hydrogen Bond Acceptor Count	11
Rotatable Bond Count	8
Heavy Atom Count	28
Complexity	463
Defined Atom Stereocenter Count	2
SMILES	C1=CC=CC=C1C[C@H](NC(CC[C@H](N)C(=O)O)=O)C(=O)O.OC(=O)C(F)(F)F
InChi Key	VCOBIUADQLSCAH-ACMTZBLWSA-N
InChi Code	InChI=1S/C14H18N2O5.C2HF3O2/c15-10(13(18)19)6-7-12(17)16-11(14(20)21)8-9-4-2-1-3-5-9;3-2(4,5)1(6)7/h1-5,10-11H,6-8,15H2,(H,16,17)(H,18,19)(H,20,21);(H,6,7)/t10-,11-;/m0./s1
Chemical Name	(2S)-2-amino-5-[[(1S)-1-carboxy-2-phenylethyl]amino]-5-oxopentanoic acid;2,2,2-trifluoroacetic acid
HS Tariff Code	2934.99.9001
Storage	Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: Please store this product in a sealed and protected environment, avoid exposure to moisture.
Shipping Condition	Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Biological Activity

Targets	Human Endogenous Metabolite
ln Vitro	γ-Glu-Phe, γ-Glu-Met, and γ-Glu-Val are detected in sourdough using tandem mass spectrometry in MRM mode with liquid chromatography. Sourdough fermented with L contains increased quantities of γ-glutamyl dipeptides. reuteri in contrast to the controls that were artificially acidified. A crucial element in the production of γ-glutamyl dipeptides is proteolysis. When comparing type I sourdough bread to conventional bread, sourdough bread with higher quantities of γ-glutamyl dipeptides rates higher in terms of taste intensity, according to sensory evaluation. L helped the sourdough breads ferment. LTH5448 and L reuteri. The degree of the salty taste varies among reuteri 100-23, which can be attributed to variations in the content of γ-glutamyl dipeptides.
References	[1]. Synthesis of Taste-Active 纬-Glutamyl Dipeptides during Sourdough Fermentation by Lactobacillus reuteri. J Agric Food Chem. 2016 Oct 12;64(40):7561-7568. [2]. 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. [3]. Synthesis of Taste-Active γ-Glutamyl Dipeptides during Sourdough Fermentation by Lactobacillus reuteri. J Agric Food Chem. 2016 Oct 12;64(40):7561-7568.

Solubility Data

Solubility (In Vitro)

H2O: 250 mg/mL (612.25 mM)

Solubility (In Vivo)

Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples. Injection Formulations (e.g. IP/IV/IM/SC) Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] *Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin → 500 μL Saline) Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO → 100 μLPEG300 → 200 μL castor oil → 650 μL Saline) Injection Formulation 7: Ethanol : Cremophor : Saline = 10： 10 : 80 (i.e. 100 μL Ethanol → 100 μL Cremophor → 800 μL Saline) Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH → 900 μL Corn oil) Injection Formulation 10: EtOH : PEG300：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Oral Formulations Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). Oral Formulation 3: Dissolved in PEG400 Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose Oral Formulation 6: Mixing with food powders Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently.  (Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	2.4490 mL	12.2450 mL	24.4900 mL
	5 mM	0.4898 mL	2.4490 mL	4.8980 mL
	10 mM	0.2449 mL	1.2245 mL	2.4490 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.