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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.
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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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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.
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.
Medical field: comprehensive application from basic nutrition to disease treatment
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.
Food Industry: Innovative Practices of Nutritional Fortification and Functional Improvement
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.
Feed Industry: Biocatalysts for Animal Growth
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%.
Cosmetics Science: Active Factors for Skin Repair
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.
Frontier Exploration: Potential Directions for Future Applications
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 glycinate, add methanol and stir to dissolve, then add ethanol to below 10 ° C, wait for the temperature to no longer rise, and then add sodium hydroxide in advance to dissolve in methanol solution for heat preservation reaction.
Filter while hot to remove insoluble substances, collect the filtrate and add glacial acetic acid. Reduce pressure to recover methanol until dry, then add methanol and stir and disperse, cool overnight.
After filtration, collection, crystallization, washing, and drying, a mixture of copper threonine and isothreonine is prepared with a yield of 68% to 74%.
Remove copper and refine the above-mentioned copper threonine, add ammonia hydroxide solution to completely dissolve it, filter and collect the filtrate, adsorb it with 732 cation exchange resin, and then wash it with ammonia and water until the solution no longer shows color as indene.
Mix the solution, concentrate it with a thin film, add ethanol to crystallize it, refrigerate overnight, filter to crystallize it, and obtain crude DL threonine. The yield is 62% compared to 73.8%.
Take crude DL threonine, heat it with water to completely dissolve it, remove the color and filter the filtrate, add ethanol, cool overnight, filter and crystallize to obtain refined DL threonine. The yield ranges from 87% to 91.3%.
Split and refine:
Mix refined DL threonine, DL threonine, and water, slowly stir and heat to dissolve.
Cool again, add D-threonine, slowly cool, separate crystalline D-threonine, filter the crystals, and obtain D-threonine after drying.
Collect the filtrate, add the same amount of DL threonine as the separated D-threonine, maintain the total volume constant, and perform the same operation as the separation of D-threonine to obtain L-threonine.
After multiple operations, D-threonine and L-threonine can be separated.
The corresponding D-threonine crude oil and L-threonine crude oil products are combined for refining, i.e. recrystallization.
Take D-threonine and L-threonine separately, add water, heat until completely dissolved, decolorize with activated carbon, filter while hot and collect the filtrate, add ethanol and let it cool, stir regularly, precipitate into crystals, and obtain D-threonine and L-threonine fine products with yields ranging from 87.3% to 91.6%. The content of L-threonine exceeds 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 a reaction tank. Put glycine into a tank, add water, and use alkaline copper sulfate to maintain heat.
The unreacted copper salt is filtered and discarded. The filtered solution is cooled overnight, filtered and crystallized, and dried to obtain blue copper glycine.
The preparation of copper threonine is carried out in a reaction tank. Put copper glycinate into the reaction tank, add methanol, stir to dissolve, then add acetaldehyde and KOH methanol solution, stir and maintain, and filter insoluble substances.
Add glacial acetic acid to the filtered liquid, and restore the dry state of methanol under reduced pressure. Add water, stir and disperse, then let it stand overnight.
After filtration and crystallization, washing and drying, copper threonine mixed with other threonine is obtained.
L-threonine powder is separated by ion exchange and copper removal. The above-mentioned copper threonine water and ammonia water are separately placed in reaction tanks, stirred and dissolved, filtered, and taken out from the 732 cation exchange column on the filtrate, and then washed with ammonia water and deionized water in sequence.
Mix the dissolution solution, concentrate the film to 150 liters, add ethanol, stir, cool, and crystallize overnight. Rough DL threonine is obtained through filtration, crystallization, and drying.
FAQ
What is L-Threonine used for?
L-Threonine is a precursor to the amino acids glycine and serine. It acts as a lipotropic in controlling fat build-up in the liver. May help combat mental illness and may be very useful in indigestion and intestinal malfunctions. Also, threonine prevents excessive liver fat.
Is L-Threonine the same as L-theanine?
L-theanine is a glutamate analog and psychoactive amino acid found in tea. L-threonine is an essential amino acid involved in protein and neurotransmitter synthesis.
Does L-Threonine help you sleep?
Taken together, these data define threonine as a physiologically relevant, sleep-promoting molecule that may intimately link neuronal metabolism of amino acids to GABAergic control of sleep drive via the neuronal substrate of sleep homeostasis.
What foods are high in L-Threonine?
l-threonine is naturally present in several food sources, including marine products (salmon, tuba, mackerel), meat products (beef, pork, chicken), dairy products (cheese, yogurt), bean (pea, peanut, almond), grain products (soybean, tofu, miso), corn, egg, and milk.
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