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| Targets |
As a synthetic intermediate, H-Cyclopropyl-Gly-OH does not possess a specific pharmacological target in the classical sense. Its role is to serve as a building block for the incorporation of cyclopropylglycine residues into peptides and peptidomimetics. The cyclopropyl ring provides unique steric and electronic properties that can influence peptide conformation and binding to biological targets, such as enzymes or receptors, once the compound is incorporated into a larger bioactive molecule. In medicinal chemistry, cyclopropyl-containing amino acids are often used to improve the pharmacokinetic and pharmacodynamic profiles of peptide-based drugs by restricting conformational flexibility and enhancing proteolytic resistance. However, the free amino acid itself is not intended to interact with any biological macromolecule; its "target" is the peptide coupling reaction in organic synthesis, where it acts as a protected or unprotected amino acid donor. Therefore, the compound is a chemical tool rather than a pharmacologically active agent.
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| 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].
The in vitro activity of H-Cyclopropyl-Gly-OH is assessed primarily through its performance in peptide synthesis rather than in biological assays. In standard solid-phase or solution-phase peptide coupling, the compound demonstrates high coupling efficiency (typically >95%) when activated with reagents such as HATU, HBTU, or DIC/HOBt. Its reactivity is characterized by the successful formation of peptide bonds with various amino acid derivatives under mild conditions, usually at room temperature within 1-4 hours. Quality control includes HPLC purity analysis (typically ≥98%) and characterization by ¹H-NMR and mass spectrometry. The compound does not exhibit any inherent biological activity, such as enzyme inhibition or receptor binding, because the free amino and carboxylic acid groups are not optimized for interactions with biological targets. Its in vitro utility is strictly limited to the chemical synthesis domain, where it serves as a precursor for more complex molecules that may later be evaluated for bioactivity. |
| ln Vivo |
In vivo activity is not applicable for H-Cyclopropyl-Gly-OH because this compound is not intended for administration to living organisms. It is exclusively a research chemical and synthetic intermediate used in laboratory settings for peptide preparation. The compound is not formulated for any route of administration, and no animal efficacy or safety studies have been conducted with the free amino acid. Any biological effects that might be observed would only arise after the compound is deprotected (if protected) or incorporated into a peptide that is then tested in vivo; however, such studies are not performed with the building block itself. Its utility lies entirely in the chemical synthesis domain, and it is stored and handled under standard laboratory conditions without consideration for pharmacokinetic or pharmacodynamic properties.
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| Enzyme Assay |
The in vitro enzyme/receptor binding (non-cellular) experimental workflow for H-Cyclopropyl-Gly-OH is not based on binding assays but rather on standard peptide synthesis and characterization procedures. Typically, the compound (1.0 equivalent) is dissolved in an appropriate solvent such as DMF or dichloromethane, and a coupling reagent (e.g., HATU, 1.1 equiv.) along with a base (e.g., DIEA, 2 equiv.) is added, followed by the amine component (e.g., resin-bound or solution-phase peptide). The reaction mixture is stirred at room temperature for 1-4 hours, and progress is monitored by TLC. After completion, the product is isolated by extraction and purified by flash chromatography or recrystallization. Characterization includes ¹H-NMR, ¹³C-NMR, and high-resolution mass spectrometry to confirm structure and enantiomeric purity. HPLC with a chiral column may be used to verify the optical purity of the compound, which is critical for its use in stereoselective synthesis.
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| Cell Assay |
In vitro cell-based experimental workflows are not typically performed with H-Cyclopropyl-Gly-OH, as the compound is not intended for direct biological activity screening. However, when used as a building block in peptide synthesis, the final deprotected peptide containing the cyclopropylglycine residue may be subjected to cell-based assays to evaluate its biological activity. In such cases, the free amino acid itself is not tested; instead, the peptide is prepared, purified, and then applied to appropriate cell lines (e.g., HEK293, HeLa, or cancer cells) at concentrations ranging from 0.1 to 100 µM for 24-72 hours. Assays may include cell viability (MTT), apoptosis (Annexin V), or receptor activation (e.g., calcium flux). The protected building block is not used in these assays because its protective groups would interfere with cellular uptake and target engagement.
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| Animal Protocol |
In vivo animal experimental workflows are not applicable for H-Cyclopropyl-Gly-OH because this compound is exclusively a synthetic intermediate, not a drug candidate. There are no established animal models or in vivo protocols associated with the free amino acid. Any in vivo studies would involve the final deprotected peptide products that incorporate the cyclopropylglycine residue, rather than the building block itself. The compound is stored under standard conditions (e.g., -20°C) and handled in a fume hood with appropriate personal protective equipment. No animal handling or dosing protocols exist for this compound, and it is not used in veterinary or preclinical research as a standalone agent.
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| ADME/Pharmacokinetics |
The pharmacokinetic properties of H-Cyclopropyl-Gly-OH have not been characterized, as the compound is not intended for pharmaceutical use. Being a small zwitterionic amino acid with a molecular weight of 115.13 g/mol and a LogP of approximately -0.7 (predicted), it would be expected to have high hydrophilicity and low membrane permeability if administered. However, the compound is never administered to living systems, and any pharmacokinetic data would pertain to the deprotected peptide products rather than the building block. The compound is stable under recommended storage conditions (powder at -20°C for 3 years, 4°C for 2 years; in solvent at -80°C for 6 months or -20°C for 1 month) and is not designed for systemic exposure. No ADME (absorption, distribution, metabolism, excretion) studies have been conducted for this compound.
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| Toxicity/Toxicokinetics |
Toxicological data for H-Cyclopropyl-Gly-OH are limited because it is not a pharmaceutical agent. Standard safety precautions apply when handling this chemical: it may cause skin and eye irritation, and inhalation of dust should be avoided. The compound should be handled in a fume hood with appropriate personal protective equipment, including gloves, safety glasses, and a laboratory coat. No chronic toxicity, carcinogenicity, or reproductive toxicity studies have been conducted, as these are not relevant for a synthetic intermediate. The compound is intended for research use only and is not approved for human or veterinary applications. It is not classified as a hazardous substance under most regulatory frameworks, but standard laboratory chemical safety practices should be followed at all times.
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| References |
[1]. Luckose F, et al. Effects of amino acid derivatives on physical, mental, and physiological activities. Crit Rev Food Sci Nutr. 2015;55(13):1793-1144.
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| Additional Infomation |
H-Cyclopropyl-Gly-OH is a well-established reagent in peptide chemistry, widely used for the introduction of the cyclopropylglycine motif into peptides and peptidomimetics. The cyclopropyl ring imparts conformational constraint, which can enhance the biological activity and stability of the resulting peptides. This compound is commercially available from multiple suppliers and is typically offered with purity ≥98%. It is not a drug and has not undergone clinical trials or received regulatory approval. Its primary applications include medicinal chemistry research, particularly in the development of enzyme inhibitors, receptor agonists/antagonists, and antimicrobial peptides. The compound is also used in the synthesis of natural product analogs and in structure-activity relationship studies. It is for research use only and is not intended for diagnostic or therapeutic purposes.
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| Molecular Formula |
C5H9NO2
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|---|---|
| Molecular Weight |
115.13
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| Exact Mass |
115.063
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| CAS # |
49606-99-7
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| PubChem CID |
1501944
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| Appearance |
Typically exists as solid at room temperature
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| Density |
1.3±0.1 g/cm3
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| Boiling Point |
253.5±23.0 °C at 760 mmHg
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| Melting Point |
-300ºC
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| Flash Point |
107.1±22.6 °C
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| Vapour Pressure |
0.0±1.1 mmHg at 25°C
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| Index of Refraction |
1.560
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| LogP |
-0.31
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| Hydrogen Bond Donor Count |
2
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| Hydrogen Bond Acceptor Count |
3
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| Rotatable Bond Count |
2
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| Heavy Atom Count |
8
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| Complexity |
109
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| Defined Atom Stereocenter Count |
1
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| SMILES |
C1CC1[C@@H](C(=O)O)N
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| InChi Key |
BUSBCPMSNBMUMT-BYPYZUCNSA-N
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| InChi Code |
InChI=1S/C5H9NO2/c6-4(5(7)8)3-1-2-3/h3-4H,1-2,6H2,(H,7,8)/t4-/m0/s1
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| Chemical Name |
(2S)-2-amino-2-cyclopropylacetic acid
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| HS Tariff Code |
2934.99.9001
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| 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)
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| 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
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| 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
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *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). View More
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)] 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). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 8.6858 mL | 43.4292 mL | 86.8583 mL | |
| 5 mM | 1.7372 mL | 8.6858 mL | 17.3717 mL | |
| 10 mM | 0.8686 mL | 4.3429 mL | 8.6858 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.
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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