Serine plays a key role in many biological processes, being a building block of proteins and a precursor of various biomolecules. Characterized by its hydroxymethyl side chain, serine is not only integral to protein synthesis, but also participates in metabolic pathways, including the biosynthesis of other amino acids, nucleotides, and neurotransmitters. Its unique chemical structure facilitates various modifications to develop serine derivatives with enhanced properties and functions. These derivatives have attracted attention in multiple industrial fields, including pharmaceuticals, biotechnology, cosmetics, and food science.
Serine, also known as 2-amino-3-hydroxypropanoic acid, is a neutral aliphatic amino acid that contains a hydroxyl group. It is polar but uncharged and is abundant in silk fibroin and silk proteins. Serine can be formed from glycine through methylation or can be deaminated to form pyruvate or hydroxypyruvate. Additionally, it serves as an important precursor for the synthesis of choline and cysteine in the body. It was first isolated in 1865 from the sulfuric acid hydrolysis solution of silk. Serine is a chiral amino acid, existing in both L- and D-forms. Only the L-form is naturally occurring in proteins, while the D-form is synthesized from L-serine through the action of serine racemase. Serine can be obtained from various sources, including soybeans, brewing yeast, dairy products, eggs, fish, whey protein, legumes, meat, nuts, seafood, seeds, and whole grains. Currently, the industrial production methods for serine typically include fermentation, protein hydrolysis extraction, chemical synthesis, and enzymatic processes.
Serine has a simple but functionally important structure characterized by an amino group (-NH₂), a carboxyl group (-COOH), and a hydroxymethyl side chain (-CH₂OH). The amino group imparts basic properties, while the carboxyl group gives it acidic characteristics, allowing serine to exist as a zwitterion at physiological pH. This zwitterionic state enhances its water solubility and facilitates its role in biochemical reactions. The polar hydroxymethyl side chain is particularly noteworthy, as it enables serine to engage in hydrogen bonding, crucial for interactions with other biomolecules. With a molecular weight of 105.09 g/mol, serine is among the smaller amino acids, contributing to its versatility in protein structures. Its high solubility in water allows it to easily dissolve in biological fluids, facilitating transport and function. At physiological pH (around 7.4), serine primarily exists in its zwitterionic form, which enhances its stability. Additionally, the presence of the hydroxyl group enables serine to undergo post-translational modifications, such as phosphorylation, which is vital for regulating protein function and signaling pathways. These structural features and properties establish serine as a critical amino acid in biological systems and industrial applications, playing essential roles in protein synthesis, metabolic pathways, and cellular signaling.
Fig. 1. Structure of serine.
Serine is a versatile amino acid with numerous health benefits, including supporting neurotransmitter production, maintaining cellular integrity, enhancing immune function, promoting muscle growth, offering neuroprotective effects, and improving gut health. Ensuring adequate intake of serine through diet or supplementation can contribute to overall well-being and support various physiological functions.
The derivatives of serine include phosphoserine, N-acetylserine, and D-serine. Among these, phosphoserine plays a key role in cellular signal transduction, where it undergoes phosphorylation modification through the action of protein kinases, regulating protein function. N-acetylserine serves as a precursor for the synthesis of cysteine in bacteria, while D-serine acts as a neurotransmitter and plays an important role in brain function, particularly in modulating neurotransmitter systems and binding to the N-methyl-D-aspartate (NMDA) receptor. Additionally, the metabolism of serine is associated with the health of the nervous system, as it participates in the synthesis of myelin, influencing the speed and efficiency of neuronal signal transmission. Therefore, serine and its derivatives hold significant research and application value in the biomedical field.
L-serine, as a fundamental amino acid that makes up proteins, is widely used in industries such as pharmaceuticals, food, and cosmetics. The global market demand for L-serine is currently 10,000 tons per year. L-serine is classified as a non-essential amino acid and serves as an important precursor in the synthesis of intracellular biomolecules, including purines, pyrimidines, and phospholipids. It is a raw material for compounded amino acid infusions and can also be used in the light chemical industry. Additionally, due to its unique wetting and moisturizing properties, L-serine is extensively utilized in high-end cosmetics both domestically and internationally.
Name | CAS | Catalog | Price |
Fmoc-allyl-L-serine | 704910-17-8 | BAT-002020 | Inquiry |
Benzyl-O-benzyl-serine | 201209-83-8 | BAT-003900 | Inquiry |
O-Sulfo-L-serine | 626-69-7 | BAT-005713 | Inquiry |
Chloroacetyl-L-serine | 80174-65-8 | BAT-014323 | Inquiry |
Benzyl-L-serine | 17136-45-7 | BAT-003898 | Inquiry |
Fmoc-L-serine | 73724-45-5 | BAT-003845 | Inquiry |
Fmoc-O-benzyl-L-serine | 83792-48-7 | BAT-003805 | Inquiry |
Boc-L-serine | 3262-72-4 | BAT-002805 | Inquiry |
D-serine is one of the main D-amino acids in mammals, accounting for approximately one-third of the total free serine in the body. Research has found that higher animals, including humans, have regions in the central nervous system with high concentrations of D-serine, which play a crucial role as a neurotransmitter. Studies have shown that D-serine performs important functions in the corpus cavernosum of the mouse penis and the lower esophageal sphincter. Currently, it is known that humans obtain D-serine through biosynthesis, protein metabolism, diet, and the breakdown of food by intestinal bacteria. Furthermore, D-serine is also used in biotechnology for the synthesis of peptides and proteins, contributing to advancements in drug delivery systems and biopharmaceuticals.
Name | CAS | Catalog | Price |
O-Benzyl-D-serine | 10433-52-0 | BAT-003553 | Inquiry |
N-α-Acetyl-D-serine | 152612-69-6 | BAT-005928 | Inquiry |
O-Methyl-D-serine | 86118-11-8 | BAT-006964 | Inquiry |
O-Phospho-D-serine | 73913-63-0 | BAT-005711 | Inquiry |
O-Sulfo-D-serine | 19794-48-0 | BAT-006966 | Inquiry |
Fmoc-D-serine | 116861-26-8 | BAT-003722 | Inquiry |
Boc-D-serine | 6368-20-3 | BAT-002733 | Inquiry |
Z-D-serine | 6081-61-4 | BAT-003306 | Inquiry |
The applications of serine derivatives span a wide range of industrial fields, reflecting their versatility and significance. From pharmaceutical innovations to cosmetic advancements and food preservation, serine derivatives are integral to enhancing product efficacy, safety, and consumer satisfaction. As research continues to unveil new potential applications, the role of serine derivatives in industrial processes is poised to expand, driving further advancements across diverse sectors.
In the pharmaceutical sector, serine derivatives are extensively utilized in drug development and formulation. L-Serine, for instance, is integral to the synthesis of phospholipids and amino acid-based drugs. Its derivatives have been explored for their neuroprotective properties, particularly in treating neurodegenerative diseases such as Alzheimer's and Parkinson's. Additionally, serine-based compounds are being investigated for their potential to enhance the efficacy of existing drugs, improve bioavailability, and reduce side effects. Another critical application is in the development of enzyme inhibitors. Certain serine derivatives can act as competitive inhibitors for serine proteases, enzymes involved in various physiological processes. These inhibitors have therapeutic implications for conditions like hypertension, cancer, and inflammatory diseases, highlighting the significance of serine derivatives in drug design and therapy.
The biotechnology sector leverages serine derivatives in the production of enzymes, particularly proteases, which are essential in various bioprocesses. Serine proteases are widely used in laundry detergents, food processing, and the production of biofuels. Their efficiency can be enhanced through the use of serine derivatives, which act as substrates or co-factors, optimizing enzyme activity and stability. Furthermore, serine derivatives are critical in recombinant DNA technology and the production of therapeutic proteins. They serve as building blocks for synthetic peptides and proteins, which are increasingly used in therapeutics, diagnostics, and research. The incorporation of serine derivatives in peptide synthesis can improve solubility and stability, thereby enhancing the overall performance of biopharmaceuticals.
In the cosmetics industry, serine derivatives are valued for their moisturizing and skin-conditioning properties. Serine, along with its derivatives, can enhance the hydration of skin and hair, making them popular ingredients in various formulations, such as creams, lotions, and shampoos. These derivatives contribute to improved texture and skin feel, providing consumers with enhanced sensory experiences. Moreover, serine derivatives can play a role in anti-aging products. By promoting collagen synthesis and improving skin elasticity, these compounds can help in reducing the appearance of fine lines and wrinkles. As the demand for effective and natural skincare products continues to rise, the incorporation of serine derivatives offers a promising avenue for innovation in cosmetic formulations.
The food industry also benefits from serine derivatives, particularly in flavor enhancement and preservation. Certain serine derivatives can act as flavoring agents or additives, improving the taste profile of various food products. Their ability to stabilize emulsions makes them valuable in dressings, sauces, and processed foods. Additionally, serine derivatives have applications as preservatives due to their antimicrobial properties. They can inhibit the growth of spoilage microorganisms, thereby extending the shelf life of food products. The growing trend towards clean label products has prompted the exploration of natural serine derivatives as alternatives to synthetic preservatives, aligning with consumer preferences for safer and more natural food options.
Feature | Serine | Threonine |
Structure | Contains a hydroxymethyl group (-CH2OH). | Contains a hydroxyl group and an ethyl group (-C2H5OH). |
Properties | Colorless, odorless, crystalline solid; hygroscopic. | Colorless, odorless, crystalline solid; hygroscopic. |
Sources | Found in meat, dairy products, nuts, beans, and spinach. | Found in meat, dairy products, eggs, and some grains like oats and wheat. |
Synthesis | Can be synthesized from glycine and other amino acids through the serine biosynthetic pathway. | Cannot be synthesized by the human body; must be obtained from the diet. |
Classification | Non-essential amino acid. | Essential amino acid. |
Side Chain | Hydroxymethyl group (–CH2OH). | Hydroxyethyl group (–C2H5OH). |
Polarity | Polar, due to the hydroxyl group. | Polar, due to the hydroxyl group. |
Functions | Involved in protein synthesis, enzyme activity, neurotransmitter production, and cell signaling. | Plays a role in protein synthesis, energy production, and is vital for immune function. |
Applications | Used in protein production, metabolic processes, and as a substrate for phosphorylation. | Used in protein production, immune function support, and is involved in glycoprotein synthesis. |
Role in Metabolism | Participates in various metabolic pathways, including glycolysis. | Involved in energy production and is essential for proper immune function. |
Modification | Can be phosphorylated to regulate protein function. | Also can be phosphorylated, impacting signaling pathways. |
Serine is a versatile amino acid with critical functions in human health and various industrial applications. Its unique structure and properties make it an essential component in protein synthesis and metabolic pathways. With advances in production methods, serine's role in pharmaceuticals, nutraceuticals, and biotechnology continues to expand, highlighting its significance in both health and industry.
** Recommended Products **
Name | CAS | Catalog | Price |
O-Trityl-L-serine | 25840-83-9 | BAT-002155 | Inquiry |
Z-O-acetyl-L-serine | 19645-29-5 | BAT-000478 | Inquiry |
Z-O-trityl-L-serine | 1330286-53-7 | BAT-000480 | Inquiry |
O-Benzyl-DL-serine | 5445-44-3 | BAT-014325 | Inquiry |
DL-Isoserine | 565-71-9 | BAT-007230 | Inquiry |
DL-Homoserine | 1927-25-9 | BAT-007229 | Inquiry |
Fmoc-O-methyl-L-serine | 159610-93-2 | BAT-007681 | Inquiry |
Fmoc-O-trityl-D-serine | 212688-51-2 | BAT-003819 | Inquiry |
Fmoc-O-acetyl-D-serine | 608512-87-4 | BAT-003799 | Inquiry |
Fmoc-DL-isoserine | 161125-36-6 | BAT-007419 | Inquiry |
Boc-L-serine methyl ester | 2766-43-0 | BAT-002807 | Inquiry |
O-Benzyl-L-serine | 4726-96-9 | BAT-004165 | Inquiry |
Boc-D-serine methyl ester | 95715-85-8 | BAT-002735 | Inquiry |
Boc-N-methyl-L-serine | 101772-29-6 | BAT-002835 | Inquiry |
Z-D-serine benzyl ester | 53933-06-5 | BAT-003307 | Inquiry |