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H-Phe-Gly-Gly-OH

Cat No.:V35512 Purity: ≥98%
L-Phenylalanylglycylglycine is a glycine analogue.
H-Phe-Gly-Gly-OH
H-Phe-Gly-Gly-OH Chemical Structure CAS No.: 23576-42-3
Product category: Peptides
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
250mg
500mg
1g
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Product Description
L-Phenylalanylglycylglycine is a glycine analogue.
H-Phe-Gly-Gly-OH (L-Phenylalanylglycylglycine, CAS 23576-42-3) is a tripeptide composed of one L-phenylalanine and two glycine residues joined in sequence. It has a molecular formula of C₁₃H₁₇N₃O₄ and a molecular weight of 279.30 g/mol. It is a metabolite and is the substrate for the characterization of tripeptide aminopeptidase from monkey brain. It is used in biochemical research to study enzyme activity.
Biological Activity I Assay Protocols (From Reference)
Targets
H-Phe-Gly-Gly-OH targets tripeptide aminopeptidase, serving as a substrate for this enzyme. Tripeptide aminopeptidase is an enzyme that cleaves N-terminal amino acids from tripeptides. The compound is used to characterize the activity and specificity of this enzyme. It does not have a therapeutic target but is a research tool for studying protease function and peptide metabolism.
ln Vitro
Commercial ergot supplements have been made from amino acids and their derivatives. They affect the release of anabolic hormones, the availability of fuel for activity, the ability to think clearly under pressure, and the prevention of muscular damage brought on by exertion. They are regarded as advantageous synergistic food ingredients [1].
In vitro, H-Phe-Gly-Gly-OH is used as a substrate for tripeptide aminopeptidase. It is used in biochemical assays to study the activity and specificity of this enzyme. The hydrolysis of the tripeptide releases phenylalanine and glycine, which can be quantified. The compound may also be used in studies of peptide transport and metabolism. It does not exhibit significant pharmacological activities such as receptor binding or enzyme inhibition beyond its role as a substrate.
ln Vivo
H-Phe-Gly-Gly-OH is not a pharmacologically active compound and therefore does not have defined in vivo activity as a therapeutic agent. It is a metabolite. When administered to animals, it would likely be metabolized by peptidases to release phenylalanine and glycine. Its primary value remains in research, where it serves as a substrate for studying tripeptide aminopeptidase and other proteases.
Enzyme Assay
In vitro enzyme assays for H-Phe-Gly-Gly-OH are designed to measure the activity of tripeptide aminopeptidase. A standard protocol involves incubating the compound with an enzyme preparation in a suitable buffer. The hydrolysis of the tripeptide bond releases phenylalanine and glycine, which can be quantified by HPLC or mass spectrometry. The progress of the reaction can be monitored, and kinetic parameters can be determined. These assays are used to characterize the enzyme's activity and specificity.
Cell Assay
In vitro cellular assays using H-Phe-Gly-Gly-OH are limited because the compound is primarily a research reagent. However, it can be used in cell culture studies to investigate peptide transport and metabolism. Cells are cultured in media supplemented with the compound, and its uptake and hydrolysis are monitored. The effects of increased phenylalanine and glycine availability on cellular metabolism can be assessed.
Animal Protocol
In vivo animal studies with H-Phe-Gly-Gly-OH are not typically conducted for therapeutic purposes. However, it may be used in metabolic studies to investigate peptide absorption and metabolism. A typical protocol involves oral or intravenous administration of the compound to rodents. Blood and tissue samples are collected to measure phenylalanine and glycine levels, allowing assessment of the compound's bioavailability and metabolic fate.
ADME/Pharmacokinetics
As a small, hydrophilic tripeptide, H-Phe-Gly-Gly-OH is expected to be rapidly absorbed and metabolized after oral administration. It is likely hydrolyzed by peptidases in the gastrointestinal tract and plasma to release phenylalanine and glycine, which then enter the endogenous amino acid pool. The compound's pharmacokinetic properties are characteristic of small peptides, with rapid clearance and short half-life.
Toxicity/Toxicokinetics
H-Phe-Gly-Gly-OH is generally considered to have low toxicity, consistent with its composition of the endogenous amino acids phenylalanine and glycine. Acute toxicity is expected to be minimal. Standard laboratory safety precautions, including the use of personal protective equipment, are recommended. No significant systemic toxicity is anticipated at typical research doses.
References

[1]. Effects of amino acid derivatives on physical, mental, and physiological activities. Crit Rev Food Sci Nutr. 2015;55(13):1793-1144.

Additional Infomation
Phe-Gly-Gly is a tripeptide composed of one L-phenylalanine residue and two glycine residues linked together in sequence. It is a metabolite.
H-Phe-Gly-Gly-OH (L-Phenylalanylglycylglycine, CAS 23576-42-3) is a tripeptide composed of one L-phenylalanine and two glycine residues. Its molecular formula is C₁₃H₁₇N₃O₄ and its molecular weight is 279.30 g/mol. It is a metabolite and is the substrate for the characterization of tripeptide aminopeptidase from monkey brain. It is soluble in water and DMSO. It is intended for research use only.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C13H17N3O4
Molecular Weight
279.2918
Exact Mass
279.122
CAS #
23576-42-3
PubChem CID
152644
Appearance
White to off-white solid powder
Density
1.296 g/cm3
Boiling Point
667.3ºC at 760 mmHg
Flash Point
357.4ºC
Vapour Pressure
1.02E-18mmHg at 25°C
Index of Refraction
1.576
LogP
0.355
Hydrogen Bond Donor Count
4
Hydrogen Bond Acceptor Count
5
Rotatable Bond Count
7
Heavy Atom Count
20
Complexity
354
Defined Atom Stereocenter Count
1
SMILES
C1=CC=C(C=C1)C[C@@H](C(=O)NCC(=O)NCC(=O)O)N
InChi Key
NAXPHWZXEXNDIW-JTQLQIEISA-N
InChi Code
InChI=1S/C13H17N3O4/c14-10(6-9-4-2-1-3-5-9)13(20)16-7-11(17)15-8-12(18)19/h1-5,10H,6-8,14H2,(H,15,17)(H,16,20)(H,18,19)/t10-/m0/s1
Chemical Name
2-[[2-[[(2S)-2-amino-3-phenylpropanoyl]amino]acetyl]amino]acetic 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

Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
H2O : ~25 mg/mL (~89.51 mM)
DMSO : ~2 mg/mL (~7.16 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 : PEG300Tween 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).
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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 : PEG300Tween 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).
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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 3.5805 mL 17.9025 mL 35.8051 mL
5 mM 0.7161 mL 3.5805 mL 7.1610 mL
10 mM 0.3581 mL 1.7903 mL 3.5805 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.

Calculator

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An example of molarity calculation using the molarity calculator is shown below:
What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
  • Enter 350.26 in the Molecular Weight (MW) box
  • Enter 10 in the Concentration box and choose the correct unit (mM)
  • Enter 5 in the Volume box and choose the correct unit (mL)
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  • The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

Dilution Calculator allows you to calculate how to dilute a stock solution of known concentrations. For example, you may Enter C1, C2 & V2 to calculate V1, as detailed below:

What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
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  • Enter 25 into the Volume (End) box and choose the correct unit (mL)
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  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
g/mol

Molecular Weight Calculator allows you to calculate the molar mass and elemental composition of a compound, as detailed below:

Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
Instructions to calculate molar mass (molecular weight) of a chemical compound:
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Definitions of molecular mass, molecular weight, molar mass and molar weight:
  • Molecular mass (or molecular weight) is the mass of one molecule of a substance and is expressed in the unified atomic mass units (u). (1 u is equal to 1/12 the mass of one atom of carbon-12)
  • Molar mass (molar weight) is the mass of one mole of a substance and is expressed in g/mol.
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Reconstitution Calculator allows you to calculate the volume of solvent required to reconstitute your vial.

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  • The answer appears in the Volume (to add to vial) box
In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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Calculation results

Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
             (2) Be sure to add the solvent(s) in order.

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