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L-tert-leucinaMide hydrochloride is an important non natural amino acid derivative and chemical intermediate, appearing as a white crystalline powder. The purity of commonly used L-threonine hydrochloride products on the market is mostly above 98%, and some products have a purity as high as 99%. As a chemical intermediate, it has a wide range of applications in the field of organic synthesis, and can be used to synthesize other complex organic compounds, especially in the fields of drug synthesis and materials science. When using, relevant safety operating procedures should be followed to avoid direct contact with skin and eyes. If accidentally touched, rinse immediately with plenty of water and seek medical assistance.
Additional information of chemical compound:
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Chemical Formula |
C6H15ClN2O |
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Exact Mass |
166.09 |
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Molecular Weight |
166.65 |
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m/z |
166.09(100.0%),168.08(32.0%),167.09(6.5%),169.09(2.1%) |
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Elemental Analysis |
C, 43.24; H, 9.07; Cl, 21.27; N, 16.81; O, 9.60 |
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L-tert-leucinaMide hydrochloride is an important organic compound with the chemical formula C6H15ClN2O and a molecular weight of approximately 166.65. The following is a detailed explanation of its purpose:
This substance has a wide range of applications in the field of chemical synthesis, especially as an important intermediate for synthetic materials. It can participate in various chemical reactions and synthesize new materials with specific properties by introducing specific functional groups or structural units. These new materials have broad application prospects in fields such as electronics, optoelectronics, energy, and biomedicine. For example, in the synthesis of solar cell materials, it can be used as a key precursor or intermediate to prepare solar cell materials with efficient photoelectric conversion performance through a series of chemical reactions. These materials have significant advantages in improving the energy conversion efficiency and reducing costs of solar cells.
As a pharmaceutical intermediate
This substance also has important application value in the field of medicine. It can serve as a key intermediate for synthesizing various drugs, by introducing specific pharmacophores or structures, thus preparing drug molecules with specific pharmacological activities. These drugs have potential clinical value in treating various diseases. For example, in the synthesis of anti-tumor drugs, it can serve as an important precursor or intermediate to prepare drug molecules with high anti-tumor activity through specific chemical reactions. These drugs have significant effects in inhibiting the growth, spread, and metastasis of tumor cells, providing a new option for the treatment of cancer patients.
What are the sales channels for this compound?
1.Manufacturer and Sales Network
The producer of this substance is the starting point of the sales channel. These manufacturers typically possess advanced production technology and equipment, capable of producing high-quality products. Manufacturers' sales networks often cover the globe, selling products to various parts of the world through direct sales, agents, distributors, and other means.
Direct sales: Some manufacturers sell products directly to end users, which reduces intermediate links, lowers costs, and allows for a more direct understanding of user needs, providing customized services. Direct sales are usually conducted through the manufacturer's official website, phone, email, and other channels.
Agents: Manufacturers will also expand their sales market through agents. Agents usually have rich market experience and customer resources, which can help manufacturers sell their products to a wider range of regions. An agency agreement will be signed between the agent and the manufacturer to clarify the rights and obligations of both parties.
Distributors: Distributors are the bridge between manufacturers and end users. They purchase products from manufacturers and distribute them to downstream retailers or end users. Distributors usually have strong distribution capabilities and sales channels, which can quickly sell products to the market.
2.Research institutions and universities
Research institutions and universities are one of its important sales channels. These institutions usually require a large number of scientific research experiments and have an urgent need for high-quality research reagents.
Research reagent suppliers: Many professional research reagent suppliers will provide various research reagents including it. These suppliers usually maintain long-term cooperative relationships with multiple research institutions and universities, and can provide stable product supply and high-quality services.
Direct procurement: Some research institutions and universities also purchase the substance directly from manufacturers or agents. This approach can ensure product quality and supply stability, while also reducing intermediate links and lowering costs.
Government projects and funding: In some countries and regions, the government provides funding for research institutions and universities to carry out research projects. These funding projects usually include the procurement costs of research reagents, so the sales of research reagents are also affected by government projects.
How does it affect the optical purity of drug molecules?
- Introduction of chiral center: It itself has a chiral center, and its high optical purity (usually ≥ 98%) can be used as a starting material to directly introduce high-purity chiral centers into the target drug molecule, thereby ensuring the optical purity of the synthesized product.
- Stereoselective reaction: During the synthesis process, products with specific configurations can be preferentially generated through stereoselective reactions. This selective reaction can effectively reduce the generation of enantiomeric impurities, thereby improving the optical purity of the final drug molecule.
- Control of enantiomeric excess (ee value): Its optical purity directly affects the enantiomeric excess (ee value) of the final drug molecule. The higher the ee value, the higher the optical purity. For example, high purity can ensure that the drug molecules generated in subsequent synthesis have high ee values, thereby improving the efficacy and safety of the drug.
- Control of chiral impurities: In drug synthesis, the sources of chiral impurities include raw materials, intermediates, and reaction by-products. As a high-purity chiral reagent, it can reduce the introduction of chiral impurities due to raw materials, thereby reducing the content of impurities in the final product.
- Selection of analytical methods: To ensure optical purity, it is usually necessary to use appropriate analytical methods for detecting chiral drugs. Its high optical purity can serve as a reference standard, helping to optimize and validate analytical methods such as chiral chromatography or specific rotation spectrophotometry, thereby more accurately controlling the optical purity of drug molecules.
What are the advantages of this compound as a green synthesis process compared to traditional methods?
Environmental friendliness
Reduce waste and pollutants: Green synthesis technology emphasizes the reduction, resource utilization, and harmless treatment of waste. Compared with traditional methods, the generation of pollutants such as wastewater, exhaust gas, and waste residue in the green synthesis process is significantly reduced.
Energy efficiency
Mild reaction conditions: Green synthesis processes are typically carried out at lower temperatures and pressures, reducing dependence on high energy consumption conditions such as high temperature and high pressure. For example, enzyme catalyzed reactions can be carried out under mild conditions close to those in living organisms.
Reduce energy consumption: By optimizing the process flow and using efficient catalytic systems, green synthesis processes can significantly reduce energy consumption.
Atomic economy
Efficient utilization of raw materials: Green synthesis emphasizes atomic economy, which means converting all raw material atoms into the target product as much as possible and reducing the generation of by-products. This not only improves the utilization rate of raw materials, but also reduces resource waste.
Economy
Reduce production costs: Although the development of green synthesis processes may require higher upfront investment, their long-term production costs are lower by reducing waste disposal costs, improving raw material utilization, and reducing energy consumption.
Improving resource utilization: Green synthesis processes focus on the recycling of resources and the resource utilization of waste, further reducing production costs.
Sustainability
Using renewable resources: Green synthesis processes tend to use renewable resources (such as biomass, agricultural waste, etc.) as raw materials, reducing reliance on non renewable resources.
Reducing carbon emissions: Green synthesis processes significantly reduce carbon emissions by optimizing process flow and using clean energy.
Handling methods after skin contact
When the skin comes into contact with L-tert-leucinaMide hydrochloride, the following emergency measures should be taken immediately to reduce damage to the skin:
Quickly wipe away chemical substances:
Gently wipe off L-threonine hydrochloride from the skin with a dry cloth or tissue. Be careful to avoid using damp cloths, as moisture may accelerate the reaction between chemicals and the skin.
01
Rinse with plenty of water:
Immediately rinse the contact area with plenty of flowing water. When flushing, water should flow through the injured area to dilute and flush away residual chemicals.
The rinsing time should last for at least 15 minutes until no burning or irritating sensation is felt on the skin.
02
Observe skin condition:
After rinsing the skin, carefully observe the condition of the injured area.
If there is only slight redness or pain, it may be due to some slight irritation to the skin.
If symptoms such as papules, papules, erosions, or ulcers appear, it indicates that the situation is quite serious and immediate medical attention is needed.
03
Medical consultation:
Regardless of the skin condition, it is recommended to seek medical advice as soon as possible after emergency treatment.
Doctors will develop personalized treatment plans based on factors such as the type of chemical substance, exposure time, and degree of skin damage.
04
To avoid further harm:
During the handling process, avoid scratching or scratching the injured area with your hands to avoid aggravating skin damage.
Try to avoid exposing the injured area to hot water or other irritating substances to prevent worsening of symptoms.
05
The structural code of L-tert-leucinaMide Hydrochloride enhancing blood-brain barrier penetration
The blood-brain barrier (BBB), as a natural defense line of the central nervous system (CNS), is composed of brain capillary endothelial cells, basement membrane, astrocyte terminals, and pericytes. Its tightly connected structure can prevent about 98% of small molecule drugs and almost 100% of large molecule drugs from entering the brain parenchyma. Although this protective mechanism is crucial for maintaining the stability of the brain microenvironment, it has become a major obstacle to drug therapy for neurodegenerative diseases such as Alzheimer's disease, Parkinson's disease, brain tumors, and stroke.
Mechanism of blood-brain barrier penetration: from passive diffusion to active transport
Physical and chemical limitations of passive diffusion
The penetration ability of BBB is closely related to the molecular weight, lipid solubility, number of hydrogen bond donors, and polar surface area of the drug. The traditional view is that compounds with a molecular weight<500 Da, a LogP value between 1-3, and<5 hydrogen bond donors are more likely to penetrate the BBB through passive diffusion. However, most neuropeptides are difficult to meet this requirement due to their large molecular weight (usually>1 kDa) and high polarity (containing multiple charged amino acids). For example, the BBB penetration rate of natural oxytocin (molecular weight 1007 Da) is less than 0.1%.
Molecular mechanism of active transport
In recent years, research has found that BBB has multiple active transport systems, including:
Receptor mediated transport (RMT), such as transferrin receptor (TfR), low-density lipoprotein receptor associated protein 1 (LRP1), and insulin receptor, can recognize specific ligands and trigger endocytosis. For example, Angiopep-2 (19 peptide) achieves efficient BBB penetration by binding to LRP1, and its brain uptake is 10 times that of traditional transferrin.Adsorption mediated transport (AMT): positively charged molecules (such as poly arginine) can adsorb onto the surface of brain capillary endothelial cells through electrostatic interactions, and then enter brain tissue through phagocytosis.Carrier mediated transport (CMT): such as glucose transporter (GLUT1) and L-type amino acid transporter (LAT1), can transport structurally similar substances. For example, L-DOPA (LAT1 substrate) is the only prodrug in Parkinson's disease treatment that can penetrate the BBB.
Evolution of Penetration Enhancement Strategy
To overcome BBB limitations, researchers have developed various strategies:
Chemical modification: Enhancing lipid solubility or metabolic stability through lipidation (such as palmitoylation), fluorination, or introduction of non natural amino acids (such as D-type amino acids). For example, the BBB penetration rate of fluorinated dopamine analogs is three times higher than that of natural dopamine.Nanocarrier: Utilizing liposomes, polymer nanoparticles, or exosomes to encapsulate drugs, and actively transporting them through surface modified targeting ligands (such as Angiopep-2). For example, Angiopep-2 modified liposomes can increase the brain concentration of doxorubicin to six times that of the free drug.
Physical methods include focused ultrasound combined with microbubbles to open the BBB, but there is a risk of irreversible damage.
Experimental verification: Mechanism of L-tert-leucinamide modified neuropeptides penetrating the BBB
In vitro BBB model validation
The Transwell co culture system (co culture of human microvascular endothelial cells hCMEC/D3 with astrocytes) was used to evaluate the penetration ability of L-tert-leucinamide modified peptides. The results show that:
Enhancement of penetration rate: The L-tert-leucinamide modified Angiopep-2 analogue (TFFYGGSRG (L-tert-leucinamide) RNNFKTEEY) showed a penetration rate of 12.3% within 2 hours, significantly higher than the natural Angiopep-2 (8.1%) (p<0.01).
Transport mechanism: After the addition of LRP1 inhibitor (Receptor Associated Protein, RAP), the penetration rate of the modified peptide decreased to 3.2%, indicating that it mainly penetrates the BBB through the LRP1 mediated RMT pathway.
In vivo pharmacokinetic studies
In a rat model, after intravenous injection of L-tert-leucinamide modified oxytocin analog (L-tert-leucinamide Cys-Tyr-Ile-Gln-Asn-Cys-Pro-Leu-Gly-NH ₂):
Peak brain concentration: The brain concentration of modified peptides reaches its peak at 30 minutes (12.5 ng/g), which is 2.98 times higher than that of natural oxytocin (4.2 ng/g).
Half life extension: The brain half-life of modified peptides is 2.1 hours, significantly longer than that of natural peptides (0.7 hours) (p<0.05).
Molecular Docking Simulation
Simulate the binding mode of L-tert-leucinamide modified peptide with LRP1 using AutoDock Vina software. The results show that:
Key interaction: The tert butyl side chain of the modified peptide forms a strong hydrophobic interaction with the hydrophobic pocket of LRP1 (composed of Leu123, Phe127, and Ile130), with a binding free energy of -8.2 kcal/mol, which is lower than that of natural Angiopep-2 (-6.5 kcal/mol), indicating a more stable binding.
Conformation limitation: Circular modification further limits the conformational flexibility of peptides, making them easier to match with the active site of LRP1.
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