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2-Amino-2-cyclopentylacetic acid

2-Amino-2-cyclopentylacetic acid is a glycine analogue.
2-Amino-2-cyclopentylacetic acid
2-Amino-2-cyclopentylacetic acid Chemical Structure CAS No.: 933-95-9
Product category: Amino Acid Derivatives
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
5g
Other Sizes
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Product Description
2-Amino-2-cyclopentylacetic acid is a glycine analogue.
2-Amino-2-cyclopentylacetic acid, also known as cyclopentylglycine, is a glycine derivative. It is a non-proteinogenic amino acid with the molecular formula C7H13NO2 and a molecular weight of 143.18 g/mol. This compound is a cyclopentyl-substituted glycine analogue used as a building block for peptidomimetic and small molecule synthesis. The cyclopentyl group introduces steric constraints and conformational rigidity into peptide sequences, which can influence the biological activity of the resulting molecules. It is a valuable organic compound utilized in life sciences research.
Biological Activity I Assay Protocols (From Reference)
Targets
2-Amino-2-cyclopentylacetic acid has been reported as a competitive inhibitor of S-adenosylmethionine synthetase, which inhibits bacterial growth. This suggests a potential target in bacterial metabolism, specifically the enzyme S-adenosylmethionine synthetase. By inhibiting this enzyme, the compound may disrupt essential cellular processes in bacteria. As a glycine derivative, it may also interact with glycine receptors or transporters, although this has not been specifically reported for this compound. Further research is needed to fully elucidate its molecular targets.
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 activity of 2-Amino-2-cyclopentylacetic acid has been demonstrated as a competitive inhibitor of S-adenosylmethionine synthetase, leading to the inhibition of bacterial growth. This in vitro antimicrobial activity suggests its potential as a lead compound for the development of new antibacterial agents. The compound's ability to inhibit a key bacterial enzyme highlights its utility in studying bacterial metabolism. Amino acid derivatives like this one are also known to influence the secretion of anabolic hormones and fuel supply, although these effects are more associated with their use as ergogenic supplements.
ln Vivo
In vivo activity of 2-Amino-2-cyclopentylacetic acid has not been well-documented. As a research chemical, it is primarily used as a building block. Its in vitro antimicrobial activity against bacteria suggests potential in vivo efficacy, but animal studies have not been reported. The compound's role as an enzyme inhibitor would need to be validated in vivo to assess its therapeutic potential. Further studies are required to determine its pharmacokinetics and pharmacodynamics in living systems.
Enzyme Assay
In vitro enzyme assays can be used to study the mechanism of action of 2-Amino-2-cyclopentylacetic acid. A typical protocol to assess its inhibition of S-adenosylmethionine synthetase would involve incubating the enzyme with varying concentrations of the compound and its substrate, ATP, and L-methionine. The production of S-adenosylmethionine is then measured using a coupled assay or HPLC. The inhibition constant (Ki) can be determined by analyzing the enzyme kinetics in the presence of different inhibitor concentrations. This assay directly measures the compound's ability to inhibit the target enzyme.
Cell Assay
Cell-based assays for 2-Amino-2-cyclopentylacetic acid would focus on its antimicrobial activity. A standard protocol is the broth microdilution assay to determine the minimum inhibitory concentration (MIC) against various bacterial strains. In this assay, serial dilutions of the compound are prepared in 96-well plates, and a standardized inoculum of bacteria is added. The plates are incubated, and the MIC is determined as the lowest concentration of compound that visibly inhibits bacterial growth. This assay is commonly used to evaluate the antimicrobial potential of new compounds.
Animal Protocol
In vivo animal experiments for 2-Amino-2-cyclopentylacetic acid are not commonly performed. If the compound were to be tested in vivo, a mouse model of bacterial infection could be used. For example, mice would be infected with a pathogenic bacterium, and then treated with various doses of the compound administered orally or intraperitoneally. Survival rates, bacterial load in organs, and histopathological changes would be assessed to determine the compound's in vivo efficacy.
ADME/Pharmacokinetics
Pharmacokinetic properties of 2-Amino-2-cyclopentylacetic acid have not been characterized. As a research chemical, it is not intended for therapeutic use. Its molecular weight of 143.18 g/mol suggests it could be absorbed orally. However, no data on its absorption, distribution, metabolism, or excretion are available. The compound's stability and solubility would influence its formulation. Any pharmacokinetic studies would be necessary if the compound were to be developed further as a drug candidate.
Toxicity/Toxicokinetics
Toxicity data for 2-Amino-2-cyclopentylacetic acid is limited. As a research chemical, it is not intended for human use. Standard laboratory safety precautions should be followed when handling this compound. No specific information regarding acute toxicity, genotoxicity, or reproductive toxicity is available. Given its structural similarity to natural amino acids, it may have a low toxicity profile, but this has not been formally established.
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
2-Amino-2-cyclopentylacetic acid is a synthetic glycine derivative used as a building block in peptidomimetic and small molecule synthesis. It is not a drug and has no approved therapeutic indications or clinical trial history. The compound is commercially available from various chemical suppliers for research purposes only. Its primary application is in the field of medicinal chemistry for the preparation of conformationally constrained peptides. The cyclopentyl group introduces steric hindrance, which can influence the bioactivity of the resulting molecules.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C7H13NO2
Molecular Weight
143.18
Exact Mass
143.094
CAS #
933-95-9
PubChem CID
224366
Appearance
White to off-white solid powder
Density
1.1±0.1 g/cm3
Boiling Point
273.5±23.0 °C at 760 mmHg
Flash Point
119.2±22.6 °C
Vapour Pressure
0.0±1.2 mmHg at 25°C
Index of Refraction
1.497
LogP
0.7
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
3
Rotatable Bond Count
2
Heavy Atom Count
10
Complexity
130
Defined Atom Stereocenter Count
0
SMILES
O=C(C(C1CCCC1)N)O
InChi Key
XBPKRVHTESHFAA-UHFFFAOYSA-N
InChi Code
InChI=1S/C7H13NO2/c8-6(7(9)10)5-3-1-2-4-5/h5-6H,1-4,8H2,(H,9,10)
Chemical Name
2-amino-2-cyclopentylacetic 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)
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
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 6.9842 mL 34.9211 mL 69.8422 mL
5 mM 1.3968 mL 6.9842 mL 13.9684 mL
10 mM 0.6984 mL 3.4921 mL 6.9842 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

Molarity Calculator allows you to calculate the mass, volume, and/or concentration required for a solution, as detailed below:

  • Calculate the Mass of a compound required to prepare a solution of known volume and concentration
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  • Calculate the Concentration of a solution resulting from a known mass of compound in a specific volume
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)
  • Click the “Calculate” button
  • 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:
  • Enter 10 into the Concentration (Start) box and choose the correct unit (mM)
  • Enter 25 into the Concentration (End) box and select the correct unit (mM)
  • Enter 25 into the Volume (End) box and choose the correct unit (mL)
  • Click the “Calculate” button
  • 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:
  • To calculate molar mass of a chemical compound, please enter the chemical/molecular formula and click the “Calculate’ button.
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.

  • Enter the mass of the reagent and the desired reconstitution concentration as well as the correct units
  • Click the “Calculate” button
  • 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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