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L-threonine powder is an organic substance with chemical formula C4H9NO3 and molecular formula NH2-CH (COOH)-CHOH-CH3,CAS 72-19-5. White crystal or crystalline powder, containing 1/2 crystal water. Odorless, slightly sweet. Easily soluble in water, insoluble in methanol, ethanol, ether and chloroform. Stable under normal temperature and pressure. L-threonine was found in fibrin hydrolysate by W · C · Ro in 1935 and proved to be the last essential amino acid discovered. Its chemical name is α-Amino-β-Hydroxybutyric acid has four stereoisomers, and only L-type has biological activity. Threonine powder is an important nutrient enhancer, which is commonly used in food additives, feed additives, fertilizer additives, etc. It can strengthen grains, cakes and dairy products, and has the same effect as tryptophan to recover human fatigue and promote growth and development. L-threonine has water holding effect on human skin. Amino acid drugs. It is mainly used for amino acid infusion, comprehensive amino acid preparation and food nutrition fortifier.
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Chemical Formula |
C4H9NO3 |
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Exact Mass |
119 |
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Molecular Weight |
119 |
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m/z |
119 (100.0%), 120 (4.3%) |
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Elemental Analysis |
C, 40.33; H, 7.62; N, 11.76; O, 40.29 |
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L-threonine powder, as one of the eight essential amino acids for the human body, has shown wide application value in the fields of medicine, food, feed, agriculture, cosmetics, and industry due to its unique chemical structure and physiological functions.
1. Nutritional support and metabolic regulation
Protein synthesis and nitrogen balance: L-threonine is a key component of collagen, elastin, and muscle tissue, involved in protein synthesis and deposition in the body, maintaining nitrogen balance. Its hydroxyl structure can bind with oligosaccharide chains, protect cell membrane integrity, promote phospholipid synthesis and fatty acid oxidation.
Anti fatty liver effect: When used in conjunction with aspartic acid and methionine, L-threonine can reduce liver fat accumulation and improve liver function. Its iron salt preparations are used to treat anemia and heart failure.
Immune regulation: L-threonine is a limiting amino acid synthesized by immunoglobulin and T/B lymphocytes, which can enhance the antibody potency of chicks against Newcastle disease virus and enhance the body's ability to resist infection.
2. Disease treatment and adjuvant intervention
Metabolic disorders: L-threonine is involved in neurotransmitter synthesis by metabolizing glycine and one carbon units, and has an auxiliary effect on relieving symptoms of depression, amyotrophic lateral sclerosis (ALS), and multiple sclerosis (MS).
Antiviral research: German scientists found that certain threonine derivatives can interfere with AIDS virus surface proteins, prevent them from invading host cells, and provide a new path for anti HIV drug development.
Trauma repair: As a core component of compound amino acid infusion, L-threonine is used for nutritional support in postoperative, burn, and fracture patients, accelerating wound healing.
3. Raw materials for drug synthesis
L-threonine is a key intermediate in the production of monoacylamide antibiotics (a highly efficient and hypoallergenic antibiotic), and its derivatives have important value in anti infective therapy.
1. Basic nutritional reinforcement
Improvement of cereal products: In response to the problem of L-threonine deficiency in grains such as wheat and rice, adding 0.1-0.5g/kg can increase protein bioavailability and improve the insufficient amino acid intake of vegetarians. For example, the protein utilization rate of fortified bread increased by 15%.
Dairy product upgrade: Adding L-threonine to infant formula can simulate the amino acid profile of breast milk and promote the development of the infant's immune system. Research shows that infants fed with this type of formula have a 12% increase in serum IgA levels compared to those fed with regular formula.
2. Development of functional foods
Sports nutrition: L-threonine promotes muscle protein synthesis and reduces muscle breakdown after exercise. Adding 500-1000mg/bottle to sports drinks can accelerate recovery.
Elderly nutrition: In response to the decline in protein synthesis ability in the elderly, the combination of L-threonine and vitamin B12 can improve muscle mass and reduce the risk of falls. The L-threonine content in the elderly specific nutritional powder developed in Japan reaches 1.5g/100g.
3. Food preservation and flavor improvement
Antioxidant effect: L-threonine can inhibit lipid oxidation and prolong the shelf life of canned meat. Experiments have shown that adding 0.3% can extend the shelf life of canned fish by 4 months.
Fragrance enhancer: It can produce a burnt aroma when heated with glucose and is used to enhance the aroma of baked goods and seasonings.
1. Nutritional enhancement for monogastric animals
Application of pig feed: L-threonine is the second limiting amino acid in pig feed, and adding 0.1-0.2% can significantly improve daily weight gain and feed conversion rate. Its mechanism of action includes:
Promote the synthesis of small intestinal mucin proteins and maintain intestinal barrier function.
Regulate fat metabolism and reduce the incidence of nutritional diarrhea in weaned piglets.
Poultry feed optimization: Adding L-threonine to broiler feed can increase breast muscle percentage. Research has shown that a 0.15% dosage increases chest muscle production by 8% while reducing abdominal fat deposition.
2. Innovation in aquatic feed
Adding 0.3% L-threonine to the feed of South American white shrimp can significantly improve specific growth rate (SGR) and feed efficiency (FE). It enhances the expression of immune related genes, thereby increasing the ability of shrimp to resist WSSV virus by 30%.
Agricultural field: Biostimulants for green planting
1. Plant growth regulation
Enhanced stress resistance: L-threonine enhances plant drought resistance by inducing proline synthesis. After treatment with 0.5mM, the survival rate of tomato seedlings under drought stress increased by 25%.
Nutrient absorption promotion: As an amino acid chelating agent, L-threonine can increase the bioavailability of trace elements such as iron and zinc, promoting crop growth.
2. Development of biopesticides
The inhibition rate of L-threonine derivatives (such as copper threonine) on pathogenic bacteria such as cucumber downy mildew and rice blast disease is over 60%. Its mechanism of action includes disrupting cell membrane integrity and inhibiting spore germination.
1. Barrier repair and moisturizing
L-threonine enhances the intercellular lipid synthesis in the stratum corneum and improves the skin's water retention ability. Clinical tests show that the lotion containing 2% L-threonine can increase skin moisture content by 20%.
2. Anti inflammation and whitening
Anti inflammatory effect: L-threonine powder can inhibit the release of inflammatory factors such as IL-6 and TNF - α, reducing the redness and swelling symptoms of acne and sensitive skin.
Whitening and Efficiency Enhancement: As a tyrosinase inhibitor, L-threonine can reduce melanin synthesis. The formula formulated with niacinamide increased skin brightness by 1.2 color steps in Asian population testing.
Industrial applications: cornerstone molecules of biomanufacturing
1. Synthesis of amino acid derivatives
L-ornithine production: L-ornithine can be efficiently synthesized from L-threonine as a precursor through the fermentation method of Corynebacterium glutamicum, which is used for the treatment of hepatic encephalopathy.
Preparation of ε - Polylysine: As a natural food preservative, ε - Polylysine is produced by fermentation of Streptomyces, and its antibacterial spectrum covers Gram positive/negative bacteria and molds. It can extend the shelf life by 2 times in bread preservation.
2. Development of biomaterials
The hydrogel prepared by cross-linking L-threonine with sodium alginate has pH responsive drug release characteristics. In diabetes wound dressing, it can continuously release insulin for 48 hours to accelerate healing.
1. Gene editing vector
The CRISPR-Cas9 delivery system modified with L-threonine can significantly improve gene editing efficiency. Mouse experiments have shown that the success rate of liver cell targeted editing is 30% higher than that of traditional liposomes.
2. 3D bioprinting
A photocurable bioink using L-threonine as a crosslinking agent has successfully printed cartilage tissue scaffolds with vascularization potential. Its mechanical strength reaches 0.6MPa, meeting clinical transplantation needs.
3. Quantum dot synthesis
L-Threonine stabilized CdSe quantum dots exhibit high fluorescence quantum yield (80%) and low cytotoxicity in biological imaging. Its animal experiments as a tumor targeting probe have entered phase I clinical trials.
From basic nutritional support to cutting-edge biotechnology, L-threonine has become a bridge connecting the health industry and high-tech fields due to its unique chemical properties and extensive physiological functions.
The industrial production methods of L-threonine powder mainly include: ① synthesis; ② Fermentation method; ③ There are three methods of protein hydrolysis. It is now advocated to produce by fermentation.
Method 1. Direct fermentation:
1. The fermentation method is to use sugar, ammonia, homoserine as the culture medium, and refine the fermentation of glutaminus to produce L-threonine.
Using glucose as raw material, we selected the feedback inhibition and repression in the synthesis of nutrient deficient and structural analogues, and reached the acid production rate of 18 g/L for L-threonine, 14 g/L for Corynebacterium glutamicum, and 14 g/L for Cybacillus mucilaginosum. Glucose [Brevibacterium flavum, Corynebacterium glutamicum, Cybacterium mucosum, etc. → L-threonine.
2. Use Micrococcus glutamicus or Bacillus brevis, Corynebacterium to ferment sugar, ammonia, homoserine, etc., and then refine them. The concentration in the fermentation liquid can reach 5~20g/L.
3. It is prepared from crotonic acid or glycine. The product can also be obtained from glucose or starch by fermentation and refining with Escherichia coli, Brevibacterium flavum, Bacillus glutamicum or Corynebacterium crenatum as strains.
Method II: Chemical synthesis:
The L-threonine obtained by chemical synthesis is a mixture of four optical isomers, namely DL threonine. The amino acid constituting the protein is L-threonine, so it is necessary to separate the threonine from the other body, and then further carry out optical isomer resolution to obtain L-threonine.
Tobacco: BU, 22; FC,21; Synthesis: It can be obtained by hydrolyzing and refining protein (such as casein), or by synthesizing methanol and mercury acetate in acrylic acid derivatives.
Under alkaline conditions, copper glycine reacts with acetaldehyde to produce a similar aldol condensation reaction to synthesize two mixtures of threonine copper: threonine and other. According to their different stability and solubility, DL threonine can be separated from threonine by decoppering, and finally L-threonine can be separated. The production processes of small scale synthesis and scale-up are introduced as follows.
For glycine preparation, monochloroacetic acid and formaldehyde solution are mixed and cooled, and concentrated ammonia water is added to control the dropping speed. After adding ammonia water, keep it warm, reduce pressure and concentrate until crystallization occurs. The crude glycine is obtained by washing and drying. The crude glycine is added to water, heated to make it completely soluble, and decolorized by adding active carbon; Filter the filtrate, add methanol, put it in the refrigerator overnight, filter and crystallize to obtain L-threonine powder. The yield is about 60% - 68%.
Preparation of copper threonine: take copper glycine, add methanol and stir to dissolve it, then add ethanol below 10 ℃, wait for the temperature to no longer rise, then add sodium hydroxide to dissolve it in methanol solution in advance, and conduct heat preservation reaction. Filter away the insoluble matter while it is hot, collect the filtrate and add glacial acetic acid. Reduce the pressure to recover methanol until it is dry, then add methanol to stir and disperse, and then cool overnight. After filtration, collection and crystallization, washing and drying, a mixture of threonine and allothreonine copper was obtained with a yield of 68% - 74%.
Decopper and refine the above threonine copper, add ammonia hydroxide solution to dissolve it completely, filter and collect the filtrate, adsorb it with 732 cation exchange resin, and wash it with ammonia water and water until the eluent does not show color to ninhydrin. Combine the eluent, concentrate it with thin film, add ethanol to crystallize it, put it in the refrigerator overnight, filter it to crystallize, and obtain crude DL threonine. The yield was 62% - 73.8%.
Take crude DL threonine, heat it with water to make it completely soluble, decolorize and filter the filtrate, add ethanol, cool it overnight, filter and crystallize to obtain refined DL threonine. The yield is 87% - 91.3%.
Split and refine: mix the refined DL threonine, DL threonine and water, slowly stir them, and heat them to dissolve. Cool down again, add D-threonine, cool down slowly, separate crystalline D-threonine, filter and crystallize, dry to obtain D-threonine. Collect the filtrate, put the same amount of DL threonine as the resolved D-threonine, keep the total volume unchanged, and perform the same operation as the resolution of D-threonine to obtain L-threonine. After repeated operation, D-threonine and L-threonine can be separated.
The corresponding D-threonine crude product and L-threonine crude product are combined for refining, i.e. recrystallization. Take D-threonine and L-threonine respectively, add water respectively, heat them until they are completely dissolved, decolorize them with activated carbon, filter and collect the filtrate while they are hot, add ethanol to them and let them stand for cooling, stir them from time to time, and precipitate crystals to obtain D-threonine and L-threonine fine products with yields of 87.3% - 91.6%. The content of L-threonine is above 95%.
Glycine is used as raw material to react with basic copper carbonate to produce copper glycine α- H is active. Under alkaline conditions, similar cross aldol condensation reaction can occur between copper glycine and acetaldehyde to generate DL threonine copper (including threonine and red body). Then DL threonine is separated from threonine by ion exchange and copper removal. Finally, D-threonine and L-threonine are separated by induced crystallization. The reaction is as follows:
The preparation of copper glycine is carried out in the reaction tank. Glycine is put into the tank, water is added, basic copper sulfate is used for heat preservation, the unreacted copper salt is filtered and discarded, the filtrate is collected, left to cool overnight, filtered for crystallization, and dried to obtain blue copper glycine.
The preparation of copper threonine is carried out in the reaction tank. Copper glycine is put into the reaction tank, methanol is added, stirred to dissolve it, then acetaldehyde and KOH methanol solutions are added, stirred and maintained, and insoluble matters are filtered out. The filtrate is added with glacial acetic acid, and methanol is recovered to dryness under reduced pressure. Water is added, stirred and dispersed, and left overnight. Filtration and crystallization are carried out, washed and dried to obtain threonine copper mixed with other threonine.
L-threonine powder is separated by ion exchange and copper removal. The above copper threonine and ammonia water are respectively put into the reaction tank, stirred to dissolve them, filtered and taken from the 732 cation exchange column on the filtrate, and then washed with ammonia water and deionized water successively. Combine the eluent, concentrate the film to 150L, add ethanol, stir, cool and crystallize overnight. The crude DL threonine was obtained by filtering and crystallizing and drying.
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