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Uracil powder (uracile) is an organic compound with molecular formula of C4H4N2O2 and molecular weight of 112.087, CAS 66-22-8. It is a fine gray white crystalline powder. Easily soluble in hot water, dilute ammonia, slightly soluble in cold water, insoluble in ethanol and ether. Uracil is the specific base of RNA, which is equivalent to thymine (T) in DNA. It is one of the four bases of RNA. It replaces thymine in DNA during DNA transcription and matches with adenine. Thymine (T) is obtained by methylation of uracil.
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Chemical Formula |
C4H4N2O2 |
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Exact Mass |
112 |
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Molecular Weight |
112 |
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m/z |
112 (100.0%), 113 (4.3%) |
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Elemental Analysis |
C, 42.86; H, 3.60; N, 24.99; O, 28.55 |
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Uracil, as a unique base of RNA, has shown wide applications in fields such as life sciences, pharmaceutical research and development, and agricultural technology. Its core value stems from its unique chemical structure - the amino (- NH ₂) and carbonyl (C=O) groups on the pyrimidine ring endow it with the ability to participate in base pairing, enzyme catalyzed reactions, and molecular modifications.
1. RNA synthesis and functional research
It is one of the four major bases of RNA, which pairs with adenine (A) through hydrogen bonding during transcription to form an RNA single stranded structure. For example, in mRNA synthesis, the distribution density of uracil directly affects its stability and translation efficiency. Research has found that mRNA with high levels of uracil is easily degraded by intracellular nucleases, while moderate modifications (such as pseudouracylation) can significantly enhance its stability. This mechanism has been applied to the optimization design of mRNA vaccines.
2. Research on DNA repair mechanism
Uracil should not exist in DNA, but when cytosine (C) spontaneously deaminates or is affected by environmental factors such as ultraviolet radiation, it can be abnormally converted to uracil, leading to C-G base pair mutations and U-A mismatches.
Cells recognize and cleave uracil through uracil DNA glycosidase (UNG), initiating the base excision repair (BER) pathway. This process is crucial for maintaining genomic stability, and the activity detection of related enzymes has become a biomarker for early diagnosis of cancer.
3. Exploration of epigenetic regulation
Its methylation modification (such as 5-methyluracil) can regulate gene expression. In plants, uracil methylation participates in disease resistance responses by affecting the RNA interference (RNAi) pathway; In animals, uracil modification in tRNA (such as 5-methoxycarbonylmethyl uracil) can alter its binding efficiency with ribosomes, thereby regulating protein synthesis rate.
1. Core components of chemotherapy drugs
5-Fluorouracil (5-FU): As a fluorinated derivative of uracil, 5-FU specifically kills rapidly proliferating tumor cells by inhibiting thymidine synthase (TS) and blocking the production of deoxythymidine (dTMP) required for DNA synthesis. Clinical data shows that the FOLFOX regimen of 5-FU combined with oxaliplatin and calcium folinate can increase the 5-year survival rate of colorectal cancer patients to over 50%.
Capecitabine: oral prodrug, which is converted into 5-FU in vivo for adjuvant treatment of breast cancer and colorectal cancer. Its advantage lies in reducing complications of intravenous injection and improving patient compliance.
2. Development of antiviral drugs
Hepatitis B treatment: Uracil analogues (such as entecavir) inhibit virus replication by competitively binding to DNA polymerase of hepatitis B virus (HBV).
Clinical trials have shown that after 48 weeks of treatment with entecavir, the HBV DNA seroconversion rate can reach over 90%.
RNA virus inhibition: Uracil derivatives can interfere with the replication enzyme activity of viral RNA. For example, research on COVID-19 (SARS-CoV-2) has found that some uracil analogues can bind to viral RNA dependent RNA polymerase (RdRp) to block viral genome replication.
3. Immune modulators
Uracil and its derivatives can regulate T cell function. For example, low-dose uracil can promote the differentiation of regulatory T cells (Tregs), inhibit excessive immune responses, and be used for the treatment of autoimmune diseases such as rheumatoid arthritis; High dose uracil enhances anti-tumor immune response by activating effector T cells (Teff).
1. Gene editing adjuvant
In the CRISPR-Cas9 gene editing system, uracil modified sgRNA can improve its stability and targeting efficiency. Research has shown that the success rate of editing sgRNAs modified with uracil glycosylation in plant cells is 30% higher than the unmodified version. This technology has been applied to the precise editing of rice disease resistance genes (such as Xa21).
2. Plant growth regulators
Uracil nucleoside (uridine), as a precursor of cytokinin, can promote plant cell division and differentiation. For example, exogenous application of uridine can significantly increase the fruit setting rate of tomato fruits and increase the weight of individual fruits.
In addition, uracil is also involved in the response of plants to adversity such as drought and salinity. Under boron deficient conditions, the synthesis of uracil diphosphate glucose (UDPG) in plants is hindered, leading to impaired sucrose transport. However, supplementing boron can restore this process and enhance crop stress resistance.
3. herbicides and defoliants
Uracil powder derivatives (such as bromobenzonitrile) interfere with plant photosynthesis and achieve weed control by inhibiting the synthesis of D1 protein in photosystem II (PSII). This type of herbicide has a control effect of over 95% on broad-leaved weeds such as amaranth and quinoa, and is highly safe for cereal crops such as wheat and corn. In cotton cultivation, uracil defoliants can promote leaf shedding, facilitate mechanical harvesting, and improve harvesting efficiency by 20% -30%.
1. Drug intermediates
It is a key raw material for synthesizing multiple drugs. For example:
Fluorouracil: Prepared by the condensation reaction of uracil and fluoroacetate, it is a commonly used anti metabolic chemotherapy drug in clinical practice.
Cytarabine: synthesized from uracil through multiple reactions, used for the treatment of acute myeloid leukemia.
2. Synthesis of nucleic acid analogues
Modified derivatives of uracil, such as pseudouracil and 5-methyluracil, are the basis for synthesizing artificial nucleic acids, such as PNA and LNA.
These analogues have higher binding affinity and stability, and are widely used in the development of nucleic acid probes, gene chips, and antisense oligonucleotide drugs.
3. Polymer material additives
Uracil groups can be introduced into polymer chains to improve material properties. For example, polyurethane materials containing uracil have excellent biocompatibility and can be used as surface coatings for implants such as medical catheters and artificial joints, reducing the risk of postoperative infection.
1. Water pollution detection
Can serve as a biomarker for microbial metabolic activity, used to evaluate the activity of microbial communities in water bodies. By detecting the concentration of uracil in wastewater, the degradation efficiency of organic pollutants can be indirectly reflected. For example, in the treatment of industrial wastewater by activated sludge process, the degradation rate of uracil is significantly positively correlated with COD removal rate (r=0.85).
2. Authenticity assessment of food
The content of uracil and its metabolites (such as uridine) can be used to identify food types or adulteration.
For example, the content of uridine in honey is closely related to its plant source. By detecting the uridine/glucose ratio, natural honey can be distinguished from artificially blended products with an accuracy rate of over 90%.
3. Forensic toxicology analysis
The metabolites of uracil derivatives (such as 5-fluorouracil) in the body (such as alpha fluoride - β - alanine) have a long half-life and can be used as biomarkers for drug abuse or poisoning. Trace metabolites can be detected in urine using liquid chromatography-mass spectrometry (LC-MS) technology, providing scientific basis for forensic identification.
In the existing technology, the synthesis routes of uracil powder are as follows:
First, add 70 mL of fuming sulfuric acid into a 200 mL clean reaction bottle, turn on the ice machine to reduce it to 0 ℃, add 25 g of urea under stirring, and control the process temperature below 10 ℃. Add 50g of malic acid, raise the temperature by 90 degrees, stir for 3h, and adjust the pH of sodium hydroxide solution to 6. After suction filtration, 70g of light red crude product was obtained. The crude product is recrystallized with 350ml of water to obtain 50g of white uracil.
Shortcomings: This process can produce 30 tons of sulfuric acid and 50 tons of waste water per ton of uracil product. It is also a traditional production process with great environmental pressure.
The second is to add 0.16 mol of sodium methoxide and 0.26 mol of ethyl acetate into a three-necked flask with a stirrer at a temperature of 15~20 ℃. Stir for 1h, then slowly add 0.10 mol ethyl formate. Reaction at 25~30 ℃ for 3h after dropping. Get white paste mixture. Add finely ground 0.09 mol thiourea into the above flask, and then raise the temperature to 60 ℃ for reaction for 1 h. Concentrate to dry under reduced pressure, dissolve the residue with a small amount of water, then slowly add 0.25mol30wt.% hydrogen peroxide, and keep the reaction temperature at 50 ℃. After the reaction, cool the mixture to 20 ℃, adjust it to pH1 with concentrated hydrochloric acid, and crystals will be released. After filtration and washing, white crystalline powder was obtained, with a yield of 71.3%. Purity>99%. The urea route uses urea instead of thiourea, and other experimental conditions remain unchanged, and the above reaction occurs. The reaction mixture is dark reddish brown clear liquid. Cool to 20 ℃, adjust the pH with concentrated hydrochloric acid, and get a light yellow clear solution, only a small amount of flaky white precipitate is generated.
Shortcomings of route 2: Although this process overcomes the generation of a large amount of waste sulfuric acid in the traditional process, the amount of waste water increases to 40 tons of waste water per ton of product.
Uracil is the specific base of RNA, which is equivalent to thymine (T) in DNA. In the process of DNA transcription, DNA is decompressed by helicase in the nucleus, and then paired with free base pairs to form a single-stranded RNA, which becomes messenger RNA (mRNA). In this process, the base pairing principles are: A-U, C-G, T-A, G-C. One of the pyrimidine bases, which is a component of RNA together with cytosine. It is also contained in uridine diphosphate glucose and other important precursors of polysaccharides. It shows specific ultraviolet absorption (259 nanometers maximum). The main difference between RNA and DNA is the difference in sugar composition. RNA contains uracil and DNA contains thymine.
Recently, NASA scientists synthesized uracil powder, a key component of life genetic material, in a non-biological way in a simulated space environment. In recent years, scientists at NASA's Ames Research Center have been simulating the interstellar space environment. They placed the ice sample containing uracil in the simulated space environment of the laboratory, exposed to ultraviolet radiation, and finally obtained the specific base of ribonucleic acid (RNA) - uracil. Uracil is an important component of RNA and the source of life on earth.
Previously, scientists have found pyrimidine in meteorites, and this experiment has proved that pyrimidine can absorb cosmic radiation and transform into uracil in space environment. Researchers believe that at the beginning of the formation of the earth, the "cornerstone" of life may have been formed in space, and they fell to the earth, creating conditions for the origin of life. In the vast space, a similar situation may exist on any planet.
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