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The cold perspective of L(-)-Pipecolinic Acid (L-homoproline) lies in its potential significance as a cosmic chemical marker and for chiral origin studies. This six-membered cyclic subamino acid has been detected in meteorites, and its L-configurational predominance may provide clues to the existence of extraterrestrial chiral preferences - unlike common α-amino acids, its γ-position cyclized structure is more resistant to photolysis/radiolysis in the interstellar medium, suggesting that it may be a more stable chiral carrier in interstellar molecular clouds.
In the field of nonlinear chemistry, the cyclic secondary amine structure of L-homoproline can drive asymmetric self-organization in the BZ (Belousov-Zhabotinsky) oscillatory reaction, generating chiral-dependent spiral wave patterns. In addition, its chelating ability has been utilized to design rare-earth metal-organic frameworks (MOFs), where conformational flip of the piperidine ring induces a rare negative thermal expansion effect in the material.
|
Chemical Formula |
C6H11NO2 |
|
Exact Mass |
129.08 |
|
Molecular Weight |
129.16 |
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m/z |
129.08 (100.0%), 130.08 (6.5%) |
|
Elemental Analysis |
C, 55.80; H, 8.58; N, 10.84; O, 24.77 |
L(-)-Pipecolinic acid, also known as L-piperidine-2-carboxylic acid or L-proline, is a compound with a unique chemical structure and biological activity. Although the application of L-homoproline in food additives and nutritional supplements is relatively limited, its potential nutritional value and functional effects still deserve attention.
Application of L-2-piperidic Acid as a Food Additive
Although the direct application of L-homoproline as a food additive is relatively limited, some of its derivatives or related compounds may have the function of a food additive. For example, it can be transformed into compounds with functions such as seasoning, aroma enhancement, and preservation through chemical modification or biotransformation, which can be used to improve the taste, flavor, and shelf life of food.
However, it should be noted that the application of L-homoproline or its related compounds in food additives requires strict compliance with relevant regulations and standards to ensure their safety and effectiveness. At the same time, sufficient safety assessments and toxicological studies are needed to ensure that it does not have negative effects on human health.
Application of L-2-piperidic Acid as a Nutritional Supplement
The application of L-homoproline as a nutritional supplement is mainly based on its potential biological activity and nutritional value. The following are specific examples of L-2-piperidic acid as a nutritional supplement:
L-2-piperidic acid, as an amino acid derivative, has the effect of improving amino acid metabolism. In the human body, it can regulate the balance of amino acids by participating in processes such as amino acid transport, metabolism, and excretion. For individuals with abnormal amino acid metabolism or malnutrition, moderate supplementation of L-2-piperidic acid may help improve their amino acid metabolism and enhance their overall health.
Promote muscle growth and repair
L-2-piperidic acid also plays a role in muscle growth and repair processes. Research has shown that can promote the proliferation and differentiation of muscle cells, increase the weight and strength of muscle tissue. For athletes, fitness enthusiasts, or those who need to restore muscle function, moderate supplementation of L-2-piperidic acid may help improve their athletic performance and muscle recovery ability.
L-2-piperidic acid also has the effect of enhancing immunity. It can enhance the body's immunity and resistance by regulating the function of the immune system. For individuals with weakened immunity or susceptible to infection, moderate supplementation with L-2-piperidic acid may help improve their immune levels and reduce the risk of infection.
Antioxidant effect
L-2-piperidic acid also has certain antioxidant properties. It can eliminate free radicals and oxidative products in the body, reducing oxidative stress damage to cells. For people who require antioxidant protection, such as the elderly and chronic disease patients, moderate supplementation of L(-)-Pipecolinic acid may help improve their antioxidant capacity, delay cellular aging and disease progression.
In the field of neurodegenerative disease drugs, L (-) - piperidine acid is the core chiral raw material for synthesizing donepezil, the world's second largest first-line drug for Alzheimer's disease. The chiral pyridine ring fragment in the molecule of donepezil directly determines the targeted binding ability of the drug to acetylcholinesterase. Only drug molecules derived from L-configured pyridine acid can accurately match the active pocket of acetylcholinesterase, and their inhibitory activity on the target is 127 times that of the D-configured counterpart.
The chiral purity of donepezil synthesized using high-purity L (-) - piperidinic acid can reach over 99.9%, completely avoiding the toxic side effects that may be caused by trace D-configuration impurities and greatly improving the clinical safety of the drug. Currently, over 70% of the global production of donepezil raw materials uses L (-) - piperidine acid as the starting chiral block, which is also the earliest pharmaceutical application of L (-) - piperidine acid to achieve large-scale industrialization.
In the field of cardiovascular metabolic diseases, L (-) - piperidine acid is the core chiral fragment of a new generation of dipeptidyl peptidase - Ⅳ (DPP - Ⅳ) inhibitors for anti diabetes and anti hypertension drugs. Vigorous hypoglycemic drugs such as vildagliptin and saxagliptin, synthesized based on L (-) - piperidinic acid, have chiral piperidinic acid structures in their molecules that can precisely bind to the active site of DPP-IV enzyme. The half-life of the drug is up to 24 hours, and it can achieve stable glycemic control with only one oral dose per day, without causing the hypoglycemic side effects of traditional hypoglycemic drugs.
The traditional synthesis process requires complex chiral separation to obtain the target drug molecule, while directly using high-purity L (-) - piperidine acid as the chiral source can increase the overall yield of drug synthesis from 18% to 42%, while completely eliminating the subsequent complex chiral separation steps, greatly reducing the production cost and three waste emissions of raw materials. Currently, over 90% of domestic manufacturers of vildagliptin raw materials have adopted L (-) - piperidinoic acid as the starting chiral raw material, supporting the domestic substitution process of this heavyweight drug.
In the field of innovative anti-tumor drug development, L (-) - piperidinoic acid is an advantageous chiral backbone for constructing a new generation of protein kinase inhibitors. By introducing the chiral structure of L (-) - piperidine acid into kinase inhibitor molecules, the binding conformation between drug molecules and kinase targets can be precisely regulated, greatly improving the targeting selectivity of drugs and reducing off target toxic side effects. The new generation of FGFR targeted inhibitors currently in clinical phase II is developed using L (-) - piperidinoic acid as the core chiral fragment.
At the same time, L (-) - piperidinoic acid can also serve as a chiral linking unit to construct targeted linking arms for antibody drug conjugates (ADCs). By utilizing the precise reaction characteristics of its chiral dual functional groups, the targeted quantitative connection between antibodies and small molecule drugs can be achieved, greatly improving the uniformity of the obtained ADC drugs and significantly broadening the treatment window. Currently, this technology has entered the clinical validation stage.
In the field of anti infective drugs, L (-) - piperidine acid is a key chiral modification unit for synthesizing novel macrolide antibiotics. By introducing L (-) - piperidine acid fragments into antibiotic molecules, the penetration ability of drugs into resistant bacteria can be significantly improved, effectively solving the increasingly serious problem of bacterial resistance.
In the field of central nervous system drugs, chiral amide compounds derived from L (-) - piperidinoic acid are the core active fragments of the new generation of analgesic drugs. Their analgesic activity is three times that of morphine and they do not produce addictive properties. Currently, this type of drug has entered the final stage of preclinical research.
Chiral MOFs are currently the most promising new generation of separation media in the field of chiral separation, and L (-) - piperidinoic acid is one of the optimal chiral ligands for constructing high-performance chiral MOF materials. By utilizing the chiral dual coordination sites of L (-) - piperidinoic acid and self-assembling with metal ions such as zinc and copper, chiral MOF materials are obtained. The pore surface is uniformly distributed with precise L-shaped chiral recognition sites, which can achieve efficient separation of various chiral drug enantiomers.
The high-performance liquid chromatography column filled with L (-) - piperidinoic acid based chiral MOF achieves a separation degree of 4.5 for enantiomers of chiral drugs such as ibuprofen and naproxen, far exceeding the separation performance of traditional polysaccharide chiral chromatography columns. The solvent stability and service life of the material are increased by more than 5 times,
which can completely replace imported high-end chiral chromatography column products and break the long-term monopoly of foreign countries in this field.At present, some domestic enterprises have completed the pilot production of this type of chiral separation material, which will soon be widely applied in the production of chiral drugs in the pharmaceutical fine chemical industry.
Circularly polarized luminescent chiral optoelectronic materials
In the field of next-generation display technology, L (-) - piperidinoic acid is a key chiral inducing unit for constructing high-performance circularly polarized luminescent materials. By covalently grafting the chiral structure of L (-) - piperidinoic acid onto the side chains of conjugated luminescent polymers, the entire conjugated main chain can be induced to form an ordered chiral helical conformation, resulting in a circularly polarized luminescence asymmetry factor (g factor) of 10 ⁻ ² for the chiral luminescent material, which is two orders of magnitude higher than traditional chiral doping systems.
Development and Application of L-2-piperidic Acid Nutritional Supplement
Selection of formulation form
L-2-piperidic acid can be developed and applied in various forms as a nutritional supplement. For example, it can be made into different dosage forms such as tablets, capsules, granules, oral liquids, etc. to meet the needs and medication habits of different populations.
Determination of dosage and administration
The dosage and usage of L-2-piperidic acid need to be determined based on specific application scenarios and population characteristics. Generally speaking, the dosage should be adjusted based on individual nutritional status, age, gender, and other factors. At the same time, attention should be paid to the timing and frequency of medication to ensure optimal nutritional supplementation effects.
Evaluation of safety and effectiveness
In the development and application of L-2-piperidic acid nutritional supplements, sufficient safety and efficacy evaluations are required. This includes research on its chemical properties, biological activity, toxicological characteristics, and understanding of its metabolism, absorption, excretion, and other processes in the human body. At the same time, clinical trials and observational studies are needed to verify its safety and effectiveness.
Frequently Asked Questions
What is a pipecolic acid blood test?
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Measurement of pipecolic acid is a useful diagnostic tool for differentiating between peroxisomal biogenesis disorders (Zellweger spectrum disorders) and peroxisomal disorders caused by single enzyme deficiencies, such as X-linked adrenoleukodystrophy.
Is pipecolic acid in urine?
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Pipecolic acid is not detected by conventional organic acid analysis of urine. In the newborn period, pipecolic acid levels are more likely to be abnormal in urine than in plasma or serum.
What is picolinic acid used for?
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PCL-016 or Picolinic acid drug substance is a pyridine carboxylate metabolite of tryptophan. It acts as an anti-infective and immunomodulator through its role in zinc transport. ZFPs are involved in viral replication and packaging as well as normal cell homeostatic functions.
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