D-cyclopropylalanine, molecular formula C6H11NO2, CAS 121786-39-8, appears as a white to almost white crystalline powder. This pure color and crystal form not only reflect its high purity and stability, but also provide convenience for its application in laboratories and industrial production. A amino acid derivative with a unique chemical structure that plays an important role in the fields of biochemistry and organic synthesis. As an amino acid derivative with a special chemical structure, it has demonstrated its unique value in various fields such as scientific research, medicine, and agriculture. Its emergence not only provides new ideas and methods for research in related fields, but also brings revolutionary changes to practical applications. It also demonstrates potential application value in fields such as cosmetics and food additives. For example, adding it or its derivatives to cosmetics can improve the moisturizing and elasticity of the skin; Adding product or its derivatives to food can increase its nutritional value and taste.
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C6H11NO2 |
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129 |
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129 |
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m/z |
129 (100.0%), 130 (6.5%) |
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C, 55.80; H, 8.58; N, 10.84; O, 24.77 |
The process of synthesizing D cyclopropylalanine from 2-acetylamino-3-cyclopropylalanine (also known as N-acetyl-D cyclopropylalanine) mainly involves the removal of acetyl groups. The following is a simplified description of the synthesis steps:
Steps for synthesizing D-cyclopropylalanine
1. Preparation of starting materials:
Firstly, ensure that you have sufficient purity and quality of 2-acetylamino-3-cyclopropylpropionic acid (N-acetyl-D cyclopropylalanine) as the starting material. This compound can usually be obtained through specific chemical synthesis methods or commercial pathways.
2. Acetyl removal:
Acetyl removal is a crucial step in the synthesis of D cyclopropylalanine. This step can be achieved through various methods, including hydrolysis reactions and catalytic hydrogenation. The following is an example of using alkaline hydrolysis method:
Dissolve 2-acetylamino-3-cyclopropylpropionic acid in an appropriate solvent (such as ethanol or methanol).
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Add excess sodium hydroxide or potassium hydroxide solution to ensure that the reaction system is in an alkaline environment.
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Heat the mixture under reflux conditions (e.g. using a water or oil bath to the boiling point of the solvent) to promote hydrolysis reaction.
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Monitor the reaction process until the acetyl group is completely removed. This can be done through methods such as TLC (thin layer chromatography) or HPLC (high-performance liquid chromatography).
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3. Neutralization and extraction:
After the acetyl removal is completed, neutralization and extraction steps are required to separate and purify the product.
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Cool the reaction mixture to room temperature, then slowly add acid (such as hydrochloric acid or sulfuric acid) for neutralization, so that the system pH drops to neutral or slightly acidic.
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Use appropriate organic solvents (such as ethyl acetate or chloroform) to extract the product. This step can transfer the product from the aqueous phase to the organic phase.
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Dry the organic phase (such as using anhydrous sodium sulfate or magnesium sulfate), then filter to remove solid impurities.
Remove organic solvents through a rotary evaporator to obtain crude products.
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4. Purification:
Further purify the crude product to obtain high-purity D cyclopropylalanine. The purification method can be selected according to specific circumstances, such as recrystallization, column chromatography (silica gel chromatography, chiral chromatography, etc.), or crystallization.
If the recrystallization method is chosen, suitable solvents (such as methanol, ethanol, isopropanol, etc.) can be selected for dissolution and recrystallization.
If column chromatography is chosen, suitable chromatography columns and eluents can be selected for separation and purification based on the polarity and chirality of the product.
5. Characterization and analysis:
Characterize and analyze the purified product to confirm its structure and purity. Common characterization methods include nuclear magnetic resonance (NMR), mass spectrometry (MS), infrared spectroscopy (IR), and high-performance liquid chromatography (HPLC). Meanwhile, optical rotation can also be measured to confirm the chirality of the product.
6. Storage and application:
D-cyclopropylalanine in a dry, cool, and dark place to avoid its decomposition or deterioration. According to specific needs, it can be used for subsequent scientific research, drug synthesis, or other application fields.
D-Cyclopropylalanine, as an amino acid derivative with a unique cyclopropyl side chain, has shown potential application value in scientific research, pharmaceutical development, and industrial production. However, its unique chemical structure may also trigger a series of adverse reactions. The following is a detailed description of its adverse reactions:
Amino acid derivatives may cause digestive system symptoms by stimulating the gastrointestinal mucosa or interfering with metabolic pathways. For example, alanine analogues may cause reactions such as indigestion, nausea, vomiting, diarrhea, and occasionally abdominal pain. Similarly, the cyclopropyl side chain of D-Cyclopropylalanine may enhance its irritation to the gastrointestinal tract, leading to similar symptoms. In addition, some amino acid derivatives may affect the balance of gut microbiota, further exacerbating gastrointestinal discomfort.
The introduction of cyclopropyl side chains may alter the interaction between amino acids and neurotransmitter receptors, thereby triggering a neurological response. For example, cycloserine (an antibiotic containing a cyclopropyl structure), as a D-alanine analog, can non selectively antagonize NMDA receptors, interfere with glutamatergic neurotransmission, cause excitotoxicity of hippocampal CA1 neurons, and trigger psychiatric symptoms such as anxiety, depression, headache, and dizziness. Although the specific mechanism of action of D-cyclosporine is not yet clear, its structural similarity suggests that there may be similar risks, especially when used in long-term or high-dose settings.
Amino acids and their derivatives may act as haptens to trigger immune responses. For example, allergic symptoms such as rash, itching, and urticaria may occur after the use of certain medications, and some patients may even experience severe allergic reactions. The cyclopropyl side chain of D-Cyclopropylalanine may serve as a new antigenic determinant, increasing the risk of allergies, especially for individuals with sensitive constitutions.
The metabolism and excretion of amino acid derivatives may increase the burden on the liver and kidneys. For example, temporary elevation of serum alanine aminotransferase (ALT) and aspartate aminotransferase (AST) may occur after the use of some drugs, indicating abnormal liver function; Long term use may damage capillaries, leading to hypoalbuminemia, metabolic acidosis, and kidney damage. D-Cycloproline is mainly metabolized by the liver and excreted by the kidneys, so individuals with liver and kidney dysfunction may face higher risks.
In addition to the above reactions, amino acid derivatives may also affect other systems. For example, symptoms such as fatigue, muscle soreness, and joint soreness may occur after the use of certain medications; High dose use may cause serious reactions such as tachycardia, hypertension, and convulsions. The cyclopropyl side chain of D-Cyclopropylalanine may interfere with energy metabolism or ion channel function, leading to similar adverse reactions.
The cyclopropyl side chain of D-Cyclopropylalanine has high strain energy, which may enhance its interaction with biomolecules such as enzymes and receptors, leading to unexpected biological effects. For example, cyclopropyl may mimic or interfere with the metabolic pathways of natural amino acids, affecting protein synthesis or neurotransmitter balance.
D-amino acids are usually not effectively utilized by the human body and may be converted into toxic products through specific metabolic pathways. For example, the metabolic product of D-isoascorbic acid (a D-amino acid analogue) may be converted into oxalic acid, which combines with calcium to form stones and increases the risk of kidney stones. Similarly, the metabolites of D-cyclopropolanine may accumulate and cause toxicity.
The cyclopropyl side chain may act as a new antigenic determinant, activating the immune system and triggering allergic reactions. In addition, long-term use may lead to immune tolerance disruption and increase the risk of autoimmune diseases.
The incidence of adverse reactions is closely related to the dosage. For example, when the daily dose exceeds 2g, the adverse reactions of certain drugs are more pronounced; Long term use may increase the risk of liver and kidney function damage. Therefore, the use of D-cyclosporine should follow the principle of "minimum effective dose" and avoid long-term high-dose use.
Genetic background, metabolic enzyme activity, and underlying diseases may affect the occurrence of adverse reactions. For example, carriers of HLA-DQB1 * 0602 gene have a 3.2-fold increased risk of psychiatric symptoms when using cycloserine; In patients with diabetes or HIV infection, the incidence of CNS toxicity increased by 41%. Similarly, there may be individual differences in the adverse reactions of D-cyclosporine, and high-risk populations need to be screened through genetic testing or risk assessment.
D-Cyclopropylalanine may interact with other drugs, enhance or weaken efficacy, or trigger new adverse reactions. For example, when combined with fluoroquinolones, the seizure threshold of certain drugs is reduced by 58%; When used in combination with antihypertensive drugs, it may increase the risk of orthostatic hypotension. Therefore, when using D-cyclosporine, detailed medication history should be consulted to avoid potential interactions.
Before use, the patient's underlying diseases, genetic background, and medication history should be evaluated to identify high-risk populations. For example, patients with liver and kidney dysfunction, diabetes or immunodeficiency should use it with caution; Allergy tests should be conducted for individuals with sensitive constitutions. During use, regular monitoring of liver and kidney function, blood routine, and electrolyte indicators should be conducted to promptly detect abnormalities and adjust dosage.
Following the principle of "minimum effective dose", the initial dose should be low and gradually adjusted according to efficacy and tolerability. For example, the initial dose of cycloserine is 250mg twice daily, and after 2 weeks, it is adjusted to the target range (15-25 μ g/mL) based on blood drug concentration; The dose for patients with renal insufficiency (eGFR<60mL/min) is halved. Similarly, the dosage of D-Cyclopropane should be adjusted according to the individual patient's situation to avoid long-term high-dose use.
Supplementing with nutrients such as vitamin B6, vitamin E, and magnesium ions may reduce the risk of adverse reactions. For example, those with vitamin B6 levels<30nmol/L need to supplement in advance; Magnesium ion supplementation (200mg/day) can reduce the incidence of tremor by 51%. In addition, cognitive-behavioral therapy (CBT) may reduce the incidence of drug-related anxiety and improve treatment compliance.
Utilizing wearable devices, saliva detection, and AI assisted diagnosis technologies to achieve real-time warning and early intervention of adverse reactions. For example, smart wristbands monitor heart rate variability (HRV) and warn of the risk of mental symptoms when HRV<20ms; Saliva detection of 8-hydroxydeoxyguanosine (8-OHdG) levels predicts oxidative stress injury 48 hours in advance. These technologies help improve the efficiency of identifying adverse reactions and reduce the incidence of serious events.
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