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As one of the nine essential amino acids that the human body cannot synthesize, valine must be obtained through dietary sources, making its role indispensable in protein synthesis and overall health. This amino acid, characterized by its aliphatic isopropyl side chain, plays a pivotal part in muscle growth, tissue repair, and energy provision, particularly during intense physical activity. Historically discovered in 1901 from casein by German chemist Hermann Emil Fischer, valine's significance extends beyond physical benefits. Emerging research links it to various metabolic pathways and medical conditions, from insulin resistance to hematopoietic stem cell function. Consequently, understanding valine's structure, sources, and benefits is crucial for advancements in medical and nutritional sciences, making it a focal point for research in enhancing human health and managing metabolic disorders.
Valine is an α-amino acid with the chemical formula C₅H₁₁NO₂. It is one of the essential amino acids, meaning it cannot be synthesized by the human body and must be obtained through diet or supplements. Valine belongs to the branched-chain amino acids (BCAAs) family, which also includes leucine and isoleucine, and is integral to muscle metabolism, tissue repair, and overall energy production. Beyond its natural occurrence, non-natural derivatives of valine, such as modified D-valine and synthetic analogs, have found significant utility in the pharmaceutical industry, where they serve as building blocks in the synthesis of complex drug molecules. These derivatives offer enhanced properties such as increased stability, altered solubility, or modified biological activity, making them indispensable in drug design and material science applications. In various sectors, valine and its derivatives are employed as key intermediates in the production of therapeutic agents, agrochemicals, and functional polymers. The use of valine in the biosynthesis of antibiotics and the development of custom polymers for advanced materials highlights its importance in diverse industrial landscapes.
Valine is a colorless, crystalline solid that is relatively insoluble in water but soluble in alcohol. Its melting point is approximately 315 °C, making it thermally stable under typical environmental conditions. Valine is nonpolar and hydrophobic, which makes it less reactive with aqueous environments, a key feature in its ability to interact with proteins and enzymes. Valine also plays a role in gluconeogenesis (the process of producing glucose from non-carbohydrate sources) during metabolic stress, such as intense physical activity or starvation. It is catabolized into succinyl-CoA, which enters the citric acid cycle to produce ATP, a critical energy source for cells.
Structurally, valine consists of an alpha-amino group (-NH3+), an alpha-carboxyl group (-COO−), and a distinctive hydrophobic side chain, isopropyl (-CH(CH3)2), making it non-polar and water-repellent. The side chain branches off from the central alpha carbon in a "Y" shape, giving valine its classification as a branched-chain amino acid. This unique branched structure plays an important role in its biological function, particularly in muscle metabolism and energy production. In protein structures, valine's hydrophobic nature contributes to protein folding by helping to stabilize the internal core of proteins, avoiding interaction with water molecules. Its presence in hydrophobic regions of proteins is key for binding to and recognizing other hydrophobic ligands.
Fig. 1. Valine amino acid structure.
Valine is one of the three BCAAs, alongside leucine and isoleucine, and is essential for various physiological functions in the body. Here are the key benefits of valine:
Valine exists in two stereoisomeric forms: L-valine and D-valine. Both forms have distinct roles in biological and synthetic applications. In addition, valine analogs, such as isovaline, are being explored for their potential therapeutic applications. These analogs can mimic the structure and function of valine but offer distinct pharmacokinetic or biochemical properties, such as improved absorption or targeted delivery, making them valuable in drug discovery.
L-valine is the biologically active form found in proteins and is essential for human nutrition. It is primarily obtained through dietary sources such as meat, dairy, eggs, and legumes. L-valine is a key contributor to muscle metabolism, tissue repair, and the production of glucose during fasting or intense physical activity. In addition, unnatural L-valine is often used in the design and synthesis of new drug molecules, especially in the development of antibacterial, antiviral and anticancer drugs.
| Name | CAS | Catalog | Price |
| Fmoc-L-valine | 68858-20-8 | BAT-003776 | Inquiry |
| Fmoc-N-methyl-L-valine | 84000-11-3 | BAT-003788 | Inquiry |
| Boc-L-valine | 13734-41-3 | BAT-002820 | Inquiry |
| Boc-L-valine amide | 35150-08-4 | BAT-002822 | Inquiry |
| Z-L-valine amide | 13139-28-1 | BAT-003391 | Inquiry |
| Z-L-valine | 1149-26-4 | BAT-003389 | Inquiry |
D-valine, a non-natural isomer, is used in the synthesis of complex pharmaceuticals and specialized polymers. It serves as an intermediate in the chemical production of antibiotics, agrochemicals, and other fine chemicals. Its unique properties allow it to be incorporated into molecules where L-valine would not be suitable, offering alternative chemical pathways for drug synthesis.
| Name | CAS | Catalog | Price |
| N-α-Formyl-D-valine | 44898-49-9 | BAT-006024 | Inquiry |
| α-Methyl-D-valine | 53940-82-2 | BAT-005805 | Inquiry |
| Acetyl-D-valine | 17916-88-0 | BAT-003468 | Inquiry |
| Fmoc-D-valine | 84624-17-9 | BAT-003725 | Inquiry |
| Boc-D-valine | 22838-58-0 | BAT-002739 | Inquiry |
| Z-D-valine | 1685-33-2 | BAT-003311 | Inquiry |
Valine is an essential amino acid that must be obtained through dietary intake. Foods rich in valine include meat such as beef, chicken, pork, and turkey, as well as fish like salmon, tuna, and halibut. Dairy products, including milk, cheese, and yogurt, are also excellent sources of valine. Plant-based sources include legumes like lentils, beans, and peas, along with whole grains such as quinoa and brown rice. Nuts and seeds, including almonds, peanuts, and sunflower seeds, provide additional dietary sources of valine, making it accessible in various food groups.
In nature, valine is synthesized by plants and microorganisms through a biosynthetic pathway starting from pyruvate, a central metabolite in carbohydrate metabolism. This pathway involves several enzymatic steps that convert pyruvate into valine. Although humans and animals cannot synthesize valine, microorganisms and plants are essential sources of valine for ecosystems and agricultural production.
Commercial production of valine generally involves microbial fermentation and chemical synthesis methods. Microbial fermentation is the most commonly used method for producing valine. This process utilizes genetically engineered strains of microorganisms, such as Escherichia coli, Corynebacterium glutamicum, or Brevibacterium flavum. These microorganisms are cultured in a controlled environment with specific nutrients, pH, and temperature conditions. The engineered strains overproduce valine through a series of metabolic pathways. After sufficient growth and production, valine is extracted and purified from the fermentation broth using techniques like crystallization and chromatography. Chemical synthesis is another method to manufacture valine, particularly non-natural variants. This involves the chemical reaction of precursor molecules through various synthetic routes. One common method is the Strecker synthesis, wherein aldehydes react with ammonia and hydrogen cyanide, followed by hydrolysis to produce an amino acid. Another approach is the catalytic hydrogenation of α-keto acids. Chemical synthesis can offer high purity and specific isomer forms of valine required for specialized applications.
Valine, along with its analogs and derivatives, plays a pivotal role across a wide range of industries due to its unique biochemical properties. Its applications extend from health and nutrition to pharmaceuticals, biotechnology, and materials science. Valine and its non-natural derivatives offer distinct advantages in various fields, where their structural and functional diversity opens new avenues for innovation.
Valine is essential for human health, particularly in muscle growth, tissue repair, and energy production. As one of the three BCAAs, valine is commonly used in dietary supplements to promote muscle protein synthesis, especially among athletes and bodybuilders. Valine supplements are also used in clinical nutrition, providing necessary amino acids for patients with muscle-wasting conditions or liver diseases. In this context, both L-valine (the natural form) and its synthetic counterparts are integral to formulating balanced amino acid supplements that enhance recovery and endurance.
Non-natural valine derivatives are employed in the synthesis of peptide-based drugs, where they contribute to enhanced drug stability, bioavailability, and specificity. One example is the use of valine derivatives in antiviral and anticancer therapies, where modifications in valine's structure can improve the therapeutic properties of these drugs. For instance, D-valine, a non-natural enantiomer, is utilized to alter the pharmacokinetics of peptide drugs, reducing degradation by proteases and extending their half-life.
In biotechnology, valine is crucial for protein engineering and recombinant protein production. It is often incorporated into synthetic peptides and proteins to optimize their function or stability. Valine's branched structure provides hydrophobicity, which enhances the folding and stability of proteins, making it essential in the design of biopharmaceuticals and industrial enzymes. The application of valine in engineered proteins extends to enzyme production for industrial processes, such as biocatalysis and biofuel generation.
Non-natural valine derivatives are being explored for creating novel polymeric materials with tailored properties, such as improved tensile strength, flexibility, or biodegradability. These materials have potential applications in drug delivery systems, tissue engineering, and environmentally friendly packaging solutions. For example, valine-based copolymers are being studied for their use in slow-release drug delivery systems, where their biocompatibility and controlled degradation rates are highly advantageous.
1. Is valine polar or nonpolar?
Valine is classified as a nonpolar amino acid. Its side chain consists of an isopropyl group (-CH(CH3)2), which is hydrophobic and does not interact favorably with water. The lack of polar functional groups in its side chain contributes to its nonpolar nature, making valine predominantly hydrophobic.
2. Is valine acidic or basic?
Valine is neither acidic nor basic. It is considered a neutral amino acid. The side chain of valine does not possess any acidic or basic properties, and its α-carboxyl group and α-amino group are present in their standard forms under physiological conditions, maintaining a neutral overall charge.
3. Is valine hydrophobic or hydrophilic?
Valine is hydrophobic. The isopropyl side chain of valine is nonpolar and repels water, which classifies it as hydrophobic. This characteristic influences valine's behavior in proteins, where it tends to reside in the interior of protein structures away from the aqueous environment.
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