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BOC-N-methyl-L-alanine, with an appearance almost resembling a white powder, molecular formula C9H17NO4, CAS 16948-16-6. It may also have other potential application values. For example, in the field of medicine, due to its unique structure and properties, it may serve as a precursor or intermediate for certain drugs, participating in drug synthesis and modification. In addition, in fields such as agriculture and food, it may also play its unique role and advantages. As an amino cid derivative, it is also commercialized as an energy supplement. Amino cids and their derivatives have been widely studied and proven to affect the secretion of synthetic metabolic hormones, fuel supply during exercise, mental performance during stress related tasks, and prevent muscle damage caused by exercise. As one of them, it is considered a beneficial dietary substance that has a positive effect on improving exercise performance and promoting physical health.
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Chemical Formula |
C9H17NO4 |
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Exact Mass |
203 |
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Molecular Weight |
203 |
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m/z |
203 (100.0%), 204 (9.7%) |
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Elemental Analysis |
C, 53.19; H, 8.43; N, 6.89; O, 31.49 |
BOC-N-methyl-L-alanine, with its unique physical and chemical properties and broad application prospects, has shown great potential in green and environmentally friendly surfactants, new chelating agents, peptide synthesis technologies, as well as in fields such as medicine, agriculture, and food. With the continuous progress of technology and the deepening of research, it is believed that the application scope of it will be further expanded and deepened.
1. Green and environmentally friendly intermediate of mild amino acid surfactants
In the chemical industry, especially in the field of surfactants, it has demonstrated its unique value. This substance can be used to synthesize green and environmentally friendly mild amino cid surfactants. Compared to traditional organic chemical surfactants, the synthesized surfactants achieve the same or even better results in terms of cleaning, emulsification, and penetration abilities. At the same time, this surfactant does not pollute the environment, has excellent skin toning and moisturizing abilities, is harmless to human health, and is especially suitable for infants and sensitive skin. This environmentally friendly and efficient feature makes it have broad application prospects in daily chemical products, detergents, skincare products, and other fields.
2. Production of new chelating agent methylglycine diacetic acid (MGDA)
It can also be used to produce a new chelating agent, methylglycine diacetic cid (MGDA). MGDA, as a high-performance and environmentally friendly detergent ingredient, can replace the phosphorus chelating agents in traditional detergents. MGDA can naturally degrade in water, avoiding the negative impact of traditional phosphates on the environment and potential harm to human health. This characteristic makes product have important application value in the field of environmentally friendly detergents.
3. As an amino acid supplement
As an amino cid derivative, it is also commercialized as an energy supplement. Amino cids and their derivatives have been widely studied and proven to affect the secretion of synthetic metabolic hormones, fuel supply during exercise, mental performance during stress related tasks, and prevent muscle damage caused by exercise. It as one of them, is considered a beneficial dietary substance that has a positive effect on improving exercise performance and promoting physical health.
4. Application in peptide synthesis technology
In peptide synthesis technology, it also plays an important role. Since the successful development of solid-phase peptide synthesis (SPPS) by MERRIFIELD in 1963, this method has become a commonly used technique in peptide and protein synthesis through continuous improvement and refinement. BOC-N-methyl-L-alanine, as one of the protective amino acids, can effectively protect the carboxyl group of the terminal amino cid in the peptide chain, avoiding unnecessary side reactions during the synthesis process. This protective strategy can significantly improve the efficiency and accuracy of peptide synthesis, providing strong support for the research and production of peptide drugs.
5. Other potential applications
In addition to the main applications mentioned above, there may also be other potential application values. For example, in the field of medicine, due to its unique structure and properties, it may serve as a precursor or intermediate for certain drugs, participating in drug synthesis and modification. In addition, in fields such as agriculture and food, it may also play its unique role and advantages.
The specific application examples of BOC-N-methyl-L-alaine in the field of daily chemical industry are mainly reflected in the following aspects:
Synthesis of mild amino acid surfactants
Can be used to synthesize green and environmentally friendly mild amino cid surfactants. Compared to traditional organic chemical surfactants, the synthesized surfactants not only achieve the same effect, but also have strong cleaning, emulsification, and penetration capabilities, do not pollute the environment, and have excellent skin toning and moisturizing abilities. They are harmless to human health and can be applied to infants, young children, and sensitive skin. This surfactant has a wide range of applications in daily chemical products such as cleaning products, skincare products, shampoo, shower gel, etc.
Production of a new chelating agent, methyl glycine diacetic acid (MGDA)
It can also be used to produce a new chelating agent, methyl glycine diacetic cid (MGDA). MGDA can replace phosphorus chelating agents in new high-performance and environmentally friendly detergents, and can naturally degrade in water, avoiding the negative impact of traditional phosphates on the environment, which is beneficial for protecting water resources and the ecological environment. Therefore, BOC-N-methyl-L-alanine also plays an important role in environmentally friendly detergents, cleaning agents, and other products.
Application in other daily chemical products
In addition to the two main application examples mentioned above, it may also be used in the formulation of other daily chemical products, such as personal care products, oral care products, etc. In these products, it may serve as a functional ingredient or auxiliary ingredient, playing a specific role. However, the specific application situation and mechanism of action may vary depending on the product, and it is necessary to refer to the formula and instructions of the specific product.
The synthesis of BOC-N-methyl-L-alanine is mainly based on the protection reaction and methylation reaction of amino acids. Firstly, the amino group of L-alanine is protected by tert butoxycarbonyl (BOC), followed by methylation reaction, and finally the target product is obtained through hydrolysis and other steps.
Experimental steps
Raw materials: L-alanine, di tert butyl dicarbonate (Boc2O), iodomethane (CH3I), potassium hydroxide (KOH), tetrahydrofuran (THF), tetrabutylammonium bisulfate (TBSA), dimethyl sulfate (Me2SO4), etc.
Equipment: reaction bottle, stirrer, constant temperature water bath, separating funnel, rotary evaporator, etc.
(1) Dissolve L-alanine (5 g, 26.4 mmol) in tetrahydrofuran (THF, 80 mL) in a reaction flask and place it in a constant temperature water bath at 0 ℃.
(2) Add finely powdered potassium hydroxide (KOH, 10.4 g, 187 mmol) in batches and stir until completely dissolved.
(3) Slowly add di tert butyl dicarbonate (Boc2O) dropwise while stirring, maintaining the reaction temperature at around 0 ℃.
(4) After dripping, continue stirring the reaction solution at 0 ℃ for 30 minutes.
(5) Subsequently, add 50 mL of water and stir at room temperature for 5 hours.
Dilute the reaction solution obtained in the previous step with ether (100 mL) and separate the water layer.
Wash the organic layer with saturated sodium bicarbonate solution (NaHCO3, 2 x 40 mL) to remove residual acid.
Dry the washed organic layer with anhydrous sodium sulfate (Na2SO4), filter it, and concentrate it to dryness using a rotary evaporator.
Dissolve tetrahydrofuran (THF) in the obtained concentrate and place it in a constant temperature water bath at 0 ℃.
Add tetrabutylammonium bisulfate (TBSA, 0.5 g, 10 wt%) as a phase transfer catalyst.
Slowly add a mixed solution of iodomethane (CH3I) and dimethyl sulfate (Me2SO4) while stirring, maintaining the reaction temperature at around 0 ℃.
After dripping, continue stirring the reaction solution at 0 ℃ for 30 minutes.
(1)
After stirring at room temperature for 5 hours, add 20% ammonium hydroxide aqueous solution (20 mL) to neutralize excess cid.
(2)
Dilute the reaction solution again with ether (100 mL) and separate the water layer.
(3)
The organic layer was acidified with 1M potassium hydrogen sulfate (KHSO4) solution to a pH of 1, and extracted with ethyl acetate (2 × 200 mL).
(4)
Merge the organic layers, dry with anhydrous sodium sulfate (Na2SO4), filter, and concentrate to dryness using a rotary evaporator.
Through the above experimental steps and corresponding chemical equations, we can clearly understand the laboratory synthesis method of product. This method is based on the protection reaction and methylation reaction of amino acids, and through precise operation and control, high-purity target products can be obtained. In practical operation, it is necessary to pay attention to the selection and control of reaction conditions to ensure the efficiency and safety of the reaction.
BOC-N-methyl-L-alaine, English name boc-N-methyl-L-alanine, CAS number 16948-16-6, molecular formula C9H17NO4, molecular weight 203.2356, is a commonly used chemical intermediate. In addition, BOC-N-methyl-L-alanine can be used not only for protein synthesis, but also as a flavor enhancer, preservative, and preservative in the food industry, as a pharmaceutical raw material in the pharmaceutical industry, and as a mild surfactant in the daily chemical industry. At present, the production methods of BOC-N-methyl-L-alanine mainly include chemical synthesis, hydrolysis extraction, enzymatic conversion, and microbial fermentation. The quality of BOC-N-methyl-L-alanine produced by chemical synthesis method is poor, and the production process is prone to environmental pollution; The hydrolysis extraction method has a complex production process and is not suitable for large-scale and industrial production.
BOC-N-methyl-L-alanine can be used as an intermediate for the synthesis of environmentally friendly mild amino acid surfactants. Compared to traditional organic chemical surfactants, the synthesized surfactants not only achieve the same effect, but also have strong cleaning, emulsification, and penetration capabilities, do not pollute the environment, and have excellent skin toning and moisturizing abilities. They are suitable for infants, young children, and sensitive skin for human health. BOC-N-methyl-L-alanine can be used to produce a new chelating agent, methyl glycine diacetic acid (MGDA), which can replace the phosphorus containing chelating agent in new high-performance environmentally friendly detergents. It can naturally degrade in water, avoiding the negative impact of traditional phosphates on the environment and avoiding harm to human health and the environment. BOC-N-methyl-L-alanine can also be used to synthesize polyesteramides, a new biodegradable polymer that can be used to produce various materials with customized properties. BOC-N-methyl-L-alanine can also be used as a catalyst to catalyze aldol condensation reactions, and the catalyst can be reused more than 5 times.
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BOC-N-methyl-L-alanine represents a pivotal tool in peptide chemistry, bridging the gap between synthetic flexibility and biological functionality. Its role in enhancing peptide stability, modulating activity, and enabling stereochemical control underscores its importance in drug discovery and materials science. While challenges in synthesis and cost remain, ongoing research into green chemistry, advanced engineering, and therapeutic applications promises to expand its utility in the coming decades.
As the demand for precision-engineered peptides grows, BOC-N-methyl-L-alanine will continue to be at the forefront of innovation, driving breakthroughs in medicine, biotechnology, and beyond.
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