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D-Alloisoleucine is an unnatural amino acid, which is opposite to the configuration of L-neneneba isoleucine. Generally white crystalline, it can be amorphous powder or colorless crystals, with a bitter and odorless taste. Molecular formula: C6H13NO2, CAS 1509-35-9. It is a solid substance in its solid form at room temperature. Poor solubility in water. It is soluble in polar solvents such as alcohol, alcohol, and ketone solvents. In non-polar solvents such as benzene and Petroleum ether, the solubility is lower. Having amine and carboxyl groups, it can form salts.
For example, it can react with Mineral acid such as hydrochloric acid to form salt. It is an optically active substance with chirality.Its optical rotation depends on concentration, solvent, and wavelength. It is right-handed and its optical rotation is ([ α] D) The value of may vary under different conditions. It can combine with water molecules to form hydrates. These water molecules can interact with functional groups in D-type molecules in the form of hydrogen bonds. Widely present in organisms, especially in bacteria and fungi.
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Chemical Formula |
C6H13NO2 |
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Exact Mass |
131 |
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Molecular Weight |
131 |
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m/z |
131 (100.0%), 132 (6.5%) |
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Elemental Analysis |
C, 54.94; H, 9.99; N, 10.68; O, 24.39 |
It is a component of bacterial cell wall synthesis and also participates in many metabolic pathways and signal transduction pathways. In addition, D-neneneba isoleucine also has pharmacological effects, such as antibacterial and anti-tumor activities, which can be used to treat some infectious and tumor diseases.
D-Alloisoleucine (CAS number 1509-35-9) is an amino acid with a unique stereoconfiguration, with the molecular formula C6H13NO2 and a molecular weight of 131.17. As the D-type enantiomer of isoleucine, it exhibits diverse application values in the food industry, covering multiple fields such as nutritional enhancement, functional food development, special dietary design, and food processing assistance.
Nutritional enhancement: compensating for dietary deficiencies and enhancing the nutritional value of food
1. Targeted supplementation of restricted amino acids
It is one of the essential amino acids for the human body, but cannot be synthesized by itself and must rely on exogenous intake. In cereal based foods (such as wheat flour and gluten) and plant proteins (such as peanut flour and potatoes), isoleucine content is low and belongs to restrictive amino acids. Its deficiency directly affects the bioavailability of protein. By adding, the content of isoleucine in food can be significantly increased, the proportion of amino acid composition can be optimized, making it closer to the human body's demand pattern, thereby enhancing the nutritional value of protein.
2. Nutritional support for special populations
Supplementation is of great clinical significance for special populations such as postoperative rehabilitation patients, the elderly, athletes, and vegetarians. As a member of branched chain amino acids (BCAAs), it works synergistically with leucine and valine to promote muscle protein synthesis, accelerate wound healing, reduce muscle breakdown, and regulate blood glucose levels. In clinical nutritional support, it is often used to prepare high branched chain amino acid formula foods for enteral or parenteral nutritional support in patients with cirrhosis, burns, trauma, and other conditions. For example, in a certain brand of medical nutrition powder, its addition amount reaches 12%.
3. Optimization of low protein diet
In the management of diseases such as chronic kidney disease that require restriction of protein intake, increasing the utilization rate of essential amino acids and reducing the intake of non essential amino acids can maintain normal metabolic function of the body while reducing total protein intake. Research has shown that adding 0.1g/kg/d to a low protein diet (0.6g/kg/d) can maintain stable serum albumin levels in patients, while reducing the accumulation of uremic toxins and delaying renal function deterioration.
Functional food development: endowing food with health attributes to meet consumer upgrading needs
1.Sports nutrition supplements
It has wide applications in the field of sports nutrition, as it can activate the mTOR signaling pathway, stimulate muscle protein synthesis, and inhibit proteolytic enzyme activity, thereby reducing muscle damage caused by exercise and accelerating post exercise recovery. In sports drinks, energy bars, and protein powders.
2. Anti fatigue functional food
It can delay the occurrence of central fatigue by regulating the synthesis of serotonin (5-HT). During prolonged high-intensity exercise, an increase in the oxidation of branched chain amino acids can lead to an increase in the proportion of tryptophan entering the brain, thereby promoting the synthesis of 5-HT and causing fatigue. Supplementing competitively inhibits the transport of tryptophan, reduces the generation of 5-HT, and thus delays fatigue. Based on this mechanism, it is widely used in anti fatigue beverages, energy gels, and dietary supplements. For example, in a certain brand of anti fatigue capsules, each capsule contains 200mg of the substance.
3. Weight management auxiliary foods
It can enhance satiety, reduce energy intake, and promote fat oxidation by regulating the secretion of energy metabolism related hormones such as glucagon like peptide-1 (GLP-1). In meal replacement foods, weight loss drinks, and dietary supplements, D is often combined with dietary fiber, protein, and other ingredients to form a low calorie, high satiety formula. For example, in a certain brand of meal replacement powder, 1g of d-alloisoleucine was added per serving. After continuous consumption for 4 weeks, the average weight of the subjects decreased by 3.2kg, waist circumference decreased by 2.8cm, and no muscle loss occurred.
Special Dietary Design: Meeting Specific Health Needs and Expanding the Boundaries of Food Applications
Infant formula food
The addition of infant formula is crucial for supporting the growth and development of infants. As an essential amino acid, it participates in key physiological processes such as protein synthesis, immune function regulation, and neural development. According to the National Food Safety Standard for Infant Formula Food (GB 10765-2021), the content of infant formula food should not be less than 4.5% of total amino acids, and it should maintain an appropriate ratio with leucine and valine. For example, in a certain brand of infant formula, the added amount is 0.18g/100kcal, which is close to the composition ratio of branched chain amino acids in breast milk.
Nutritional foods for the elderly
As people age, their protein synthesis ability decreases and muscle mass decreases (sarcopenia), leading to an increased risk of falls. Its supplementation can delay the progression of sarcopenia by stimulating muscle protein synthesis. In nutritional foods for the elderly, dalloisoleucine is often combined with whey protein, vitamin D, and other ingredients to form a specialized formula for the elderly population. For example, in a certain brand of elderly nutrition powder, adding 0.8g per serving, after continuous consumption for 3 months.
Special food for diabetes
By regulating the activity of glucose metabolism related enzymes, insulin sensitivity can be improved, and glycogen synthesis can be promoted to assist in controlling blood glucose levels. In diabetes food, it is often compounded with low GI carbohydrate, dietary fiber and other ingredients to form a formula of low GI and high branched chain amino acids. For example, when 0.3g is added to a brand of bread dedicated to diabetes every 100g, the peak postprandial blood glucose of the subjects will be reduced by 20%.
Food processing assistance: improving food quality and enhancing processing efficiency
1. Food flavoring agents
It has a slight bitterness and freshness, and can be used as a flavor enhancer to enhance the flavor of food. The addition of d-alloisoleucine in seasonings, soups, and meat products can enhance the richness and freshness of food, and mask some unpleasant odors.
For example, in a certain brand of chicken essence seasoning, adding 0.05% dalloisoleucine increased the umami intensity by 15% and reduced the bitterness perception threshold by 20%.
2. Food stabilizers
Its amino and carboxyl groups can form stable structures with other components in food, such as proteins and polysaccharides, through hydrogen bonding, ionic bonding, and other interactions, thereby improving the texture and stability of food. In dairy products, beverages, and baked goods, adding can prevent protein precipitation, polysaccharide degradation, and fat floating, extending the shelf life of products. For example, in a certain brand of yogurt, adding 0.02% dalloisoleucine reduces whey precipitation by 30%.
3. Food antioxidants
It can exert antioxidant effects by chelating metal ions (such as Fe ² ⁺, Cu ² ⁺), scavenging free radicals, and inhibiting lipid peroxidation. Adding it to fats, fried foods, and nut products can delay the oxidation and rancidity of fats, and maintain the color and flavor of the food. For example, in a certain brand of peanut oil, after adding 0.01% dalloisoleucine, the peroxide value (POV) decreased by 40% and the induction period was extended by 50% in an accelerated storage test at 60 ℃.
D alloisoleucine, as a multifunctional amino acid, has shown broad application prospects in the food industry. From nutritional enhancement to functional food development, from special dietary design to food processing assistance, through scientific proportioning and precise addition, it not only enhances the nutritional value and health attributes of food, but also meets consumers' demand for high-quality and personalized food.
synthetic methods
It (D-neneneba isoleucine) is an unnatural amino acid, which can be obtained by a variety of synthetic methods.
Optical resolution method is one of the most common methods for synthesizing d alloisoleucine. This method uses chiral compounds to react with Chiral resolution reagents to produce an optical isomer mixture, and then the target product is separated and purified from the mixture by crystallization, chromatography and other means. For example, the synthesis of alloisoleucine can be obtained by optical separation of L-neneneba isoleucine and Chiral resolution reagents.
The catalyst method is also widely used for the synthesis of product. This method typically utilizes chiral catalysts to catalyze the reaction of ketones or aldehydes with amines, forming chiral amino acids. For example, chiral metal complexes can be used as catalysts to generate product in the presence of ketone or aldehyde substrates and amine substrates.
Enzymatic catalysis is a mild and efficient method for synthesizing product. Enzymatic catalysis usually utilizes enzymes such as amino acid enzymes or transaminases to catalyze the conversion reaction of substrates. By selecting appropriate enzyme catalysts and reaction conditions, it can be selectively synthesized.
Chemical synthesis is a commonly used method for synthesizing product, which can gradually construct target molecules through multi-step reactions. This method involves a variety of organic synthesis technologies, such as Substitution reaction, Condensation reaction and protective group strategy. The specific chemical synthesis routes may vary depending on researchers and laboratories, but the basic steps include selective substitution of ketones or aldehydes, chemical resolution, and chiral induction.
It should be noted that during the synthesis of product, attention should be paid to the selection of appropriate substrates, catalysts and reaction conditions to obtain products with high yield and high Stereoselectivity. In addition, the purification and separation process is also very important, and products can be purified and separated using methods such as chromatography, crystallization, and washing.In summary, there are various synthesis methods for it, and suitable methods can be selected according to specific needs. When designing and optimizing synthesis routes, it is necessary to comprehensively consider factors such as synthesis efficiency, synthesis cost, chiral control, and environmental friendliness to obtain high-quality D Alloisoleucine.
FAQ
D Alloisoleucine is a rare unnatural chiral amino acid, belonging to the stereoisomer of L-isoleucine. It has a unique branched aliphatic molecular structure with stable stereochemical configuration, good chemical purity and structural stability. It is commonly used as a key chiral building block in peptide synthesis, pharmaceutical intermediate derivation and biochemical mechanism research, and plays an important role in the development of bioactive peptides and chiral drug molecules.
Mainly used for chiral pharmaceutical synthesis, peptide compound preparation and biochemical research.
As an amino acid powder, D Alloisoleucine is easily affected by moisture and high temperature, which may cause agglomeration and purity decline. It should be stored in a sealed, dry, cool and dark environment, away from humid air, strong oxidants and high-temperature heat sources. During weighing and use, operate in a dry environment to prevent moisture absorption, so as to maintain its optical purity and chemical stability for long-term use.
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