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| Targets |
As a glycine derivative with a tert-butyl ester protecting group, H-Gly-OtBu·HCl does not have a specific biological target. Its primary utility is as a chemical building block in organic synthesis, particularly in peptide chemistry. The compound serves as a protected glycine unit that can be incorporated into peptide chains while preventing unwanted reactions at the carboxyl terminus. The tert-butyl ester group provides steric hindrance and acid-labile protection, allowing for selective deprotection during peptide assembly. In biological systems, the ester can be hydrolyzed to release glycine, which is an important neurotransmitter and metabolic precursor. However, in its protected form, the compound is not designed to interact with biological receptors or enzymes in a pharmacologically meaningful way. Its value lies in its chemical properties rather than any intrinsic biological activity.
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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].
H-Gly-OtBu·HCl does not exhibit pharmacological activity in vitro. As a protected amino acid ester, it is a synthetic intermediate rather than a bioactive compound. In vitro studies using this compound typically focus on its chemical reactivity, such as its use in peptide bond formation reactions or its stability under various conditions. The compound may be used as a substrate in enzymatic assays to study esterase activity, as the tert-butyl ester can be cleaved by certain hydrolases. However, these are analytical or preparative applications rather than assessments of pharmacological activity. The compound does not bind to receptors, inhibit enzymes, or produce cytotoxic effects in cell-based assays at concentrations typically used for synthesis. Its role in research is almost exclusively as a reagent for organic synthesis. |
| ln Vivo |
H-Gly-OtBu·HCl is not a pharmacologically active compound and therefore does not have defined in vivo activity as a drug. When administered to animals, the compound would likely be hydrolyzed by esterases to release glycine, which would then enter normal metabolic pathways. The tert-butyl ester may provide enhanced lipophilicity compared to free glycine, potentially improving membrane permeability and oral absorption. However, the compound is not used therapeutically, and its in vivo effects would be limited to those of the released glycine, which is an endogenous amino acid. Nutritional or metabolic studies may employ this compound as a glycine source, but these are research applications rather than therapeutic interventions. The compound's primary value remains in synthetic chemistry.
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| Enzyme Assay |
In vitro enzyme assays for H-Gly-OtBu·HCl are typically designed to study esterase or protease activity. A standard protocol involves incubating the compound with an enzyme preparation, such as plasma, tissue homogenates, or purified carboxylesterases, in a suitable buffer at physiological pH. The hydrolysis of the tert-butyl ester releases glycine and tert-butanol, which can be quantified by HPLC, GC, or mass spectrometry. Alternatively, the decrease in substrate concentration can be monitored. The reaction is initiated by addition of the substrate, and the initial velocity is measured over time. These assays are used to characterize the substrate specificity of esterases, to screen for enzyme inhibitors, or to evaluate the stability of tert-butyl ester protecting groups in biological matrices. The compound serves as a model substrate for studying ester hydrolysis kinetics.
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| Cell Assay |
In vitro cellular assays using H-Gly-OtBu·HCl are limited due to the compound's role as a synthetic intermediate rather than a bioactive molecule. However, it can be used in cell culture studies to investigate the intracellular delivery of glycine via ester hydrolysis. Cells are cultured in media supplemented with the compound, and cellular uptake, ester hydrolysis, and glycine release are monitored. The effects of increased intracellular glycine on cellular metabolism, protein synthesis, or glutathione production can be assessed. These experiments are typically conducted in cell lines such as hepatocytes or neurons, and endpoints are measured using biochemical assays or mass spectrometry. The compound's ability to penetrate cell membranes may be enhanced by the lipophilic tert-butyl ester group, making it useful for studying glycine's intracellular functions.
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| Animal Protocol |
In vivo animal studies with H-Gly-OtBu·HCl are primarily conducted in the context of nutritional or metabolic research. A typical protocol involves oral or intraperitoneal administration of the compound to rodents at doses ranging from 10 to 500 mg/kg. Blood samples are collected at various time points to measure glycine and tert-butanol levels, allowing assessment of the compound's absorption, hydrolysis, and pharmacokinetics. The compound's ability to elevate plasma glycine concentrations and its effects on glycine metabolism, neurotransmitter levels, or liver function may be evaluated. These studies help to understand the bioavailability of amino acid esters and their utility as glycine delivery agents. The compound may also be used in studies of esterase activity and amino acid transport in vivo.
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| ADME/Pharmacokinetics |
As a glycine tert-butyl ester, H-Gly-OtBu·HCl is expected to be absorbed after oral administration, although detailed pharmacokinetic data are not well-documented. The compound is likely hydrolyzed by esterases in the gastrointestinal tract, liver, and plasma to release glycine and tert-butanol. The tert-butyl ester may enhance lipophilicity and membrane permeability compared to free glycine, potentially improving oral bioavailability. Following hydrolysis, glycine enters the endogenous amino acid pool and is distributed throughout the body via the circulation. Glycine is metabolized through various pathways, including incorporation into proteins, conversion to serine, and participation in one-carbon metabolism. The pharmacokinetic profile of the compound is primarily determined by the rate of ester hydrolysis and the subsequent metabolism of glycine.
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| Toxicity/Toxicokinetics |
The hydrochloride salt of glycine tert-butyl ester is generally considered to have low toxicity, consistent with its use as a chemical reagent and its metabolic conversion to the endogenous amino acid glycine. Acute toxicity is expected to be minimal, as glycine has a very low toxicity profile. However, the compound may cause irritation upon contact with skin, eyes, or mucous membranes due to its acidic nature. Inhalation of the powder may cause respiratory irritation. The compound is not classified as a carcinogen, mutagen, or reproductive toxicant. Standard laboratory safety precautions, including the use of personal protective equipment, are recommended. No significant systemic toxicity is anticipated at typical research doses, as the compound is rapidly metabolized to glycine and tert-butanol, the latter being a common solvent metabolite.
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| References | |
| Additional Infomation |
Glycine tert-butyl ester hydrochloride (H-Gly-OtBu·HCl, CAS 27532-96-3) is a protected amino acid derivative used as a building block in peptide synthesis. Its chemical formula is C₆H₁₃NO₂·HCl and molecular weight is 167.63. The compound appears as a white crystalline solid. It is soluble in water and polar organic solvents. The tert-butyl ester group provides acid-labile protection for the carboxyl function, allowing selective deprotection under mild acidic conditions. This compound is widely used in the synthesis of peptides and pharmaceutical intermediates. It is intended for research use only and is not for human therapeutic applications. Standard storage conditions are at room temperature in a cool, dry place.
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| Molecular Formula |
C6H14CLNO2
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| Molecular Weight |
167.6339
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| Exact Mass |
167.071
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| CAS # |
27532-96-3
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| Related CAS # |
tert-Butyl 2-aminoacetate;6456-74-2
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| PubChem CID |
2725036
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| Appearance |
White to off-white solid powder
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| Density |
0.973g/cm3
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| Boiling Point |
145.7ºC at 760mmHg
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| Melting Point |
141-143 °C(lit.)
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| Flash Point |
20.7ºC
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| Vapour Pressure |
0.026mmHg at 25°C
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| Index of Refraction |
1.522
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| LogP |
1.789
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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 |
3
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| Heavy Atom Count |
10
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| Complexity |
104
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| Defined Atom Stereocenter Count |
0
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| SMILES |
Cl[H].O(C(C([H])([H])N([H])[H])=O)C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H]
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| InChi Key |
OSWULUXZFOQIRU-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C6H13NO2.ClH/c1-6(2,3)9-5(8)4-7;/h4,7H2,1-3H3;1H
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| Chemical Name |
tert-butyl 2-aminoacetate;hydrochloride
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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) |
DMSO : ≥ 100 mg/mL (~596.55 mM)
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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 | 5.9655 mL | 29.8276 mL | 59.6552 mL | |
| 5 mM | 1.1931 mL | 5.9655 mL | 11.9310 mL | |
| 10 mM | 0.5966 mL | 2.9828 mL | 5.9655 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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