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D-Pipecolinic acid is a colorless or white crystalline powder that resembles a crystalline solid in appearance. The Molar mass is about 129.15 g/mol, CAS 1723-00-8, and the Molecular formula is C6H11NO2. It is soluble in water and its solubility is influenced by temperature and pH value. Its water solubility at room temperature is approximately 1g/10mL. In addition, it can also be dissolved in some organic solvents, such as alcohols, ethers, and ketones. Its boiling point has not been reported yet, as its decomposition temperature is relatively low.
It has extensive application value in fields such as drug synthesis, alkaloid compound synthesis, preservatives, metal chelating agents, polymer materials, coordination chemistry research, and biochemical research. Its diversity and unique properties make it an important research object in many fields of chemical and biological sciences.
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Chemical Formula |
C6H11NO2 |
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Exact Mass |
129 |
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Molecular Weight |
129 |
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m/z |
129 (100.0%), 130 (6.5%) |
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Elemental Analysis |
C, 55.80; H, 8.58; N, 10.84; O, 24.77 |
It is a thermally stable compound with a thermal decomposition temperature higher than its melting point. However, the specific thermal decomposition properties require further research and experimental determination. It is a chiral molecule with two optical isomers, D - and L -. The optical rotation of product is[ α] D+8.8 ° (concentration 1, solvent water). It has certain absorption characteristics and can absorb ultraviolet light. It is acidic and has a pKa value of approximately 4-5. In water, it ionizes to produce hydrogen ions, making the solution acidic.
D-Pipecolinic acid (CAS number: 1723-00-8) is a compound with a unique chemical structure and biological activity, which has shown wide potential applications in fields such as biochemistry, pharmaceutical science, and agricultural science. Its molecular formula is C ₅ H ₉ NO ₂, with a molecular weight of 115.13. It belongs to non protein amino acids and is an important intermediate in the lysine metabolism pathway. The following are its important uses:
Medical Applications: Dual Value of Treatment and Diagnosis
Development of antiepileptic drugs
Its mechanism of action in pyridoxine dependent epilepsy has been extensively studied. High levels of DCIP can interfere with the metabolism of gamma aminobutyric acid (GABA), leading to excessive neuronal excitation and triggering epileptic seizures. Therefore, DCIP has become an important therapeutictarget for pyridoxine dependent epilepsy. By inhibiting the activity of gamma aminobutyric acid transaminase (GABA-T) and reducing the degradation of GABA, the concentration of GABA in the brain is increased, thereby exerting an antiepileptic effect.
In response to the metabolic abnormalities of D-Pipecolic Acid, researchers have developed various inhibitors, such as 4-hydroxypipecolic acid, aimed at reducing its concentration in the body and alleviating epilepsy symptoms. In recent years, with the in-depth study of the metabolic pathway of D-Pipecolic Acid, new types of antiepileptic drugs have emerged continuously. For example, by regulating the metabolic enzymes of D-Pipecolic Acid, more precise therapeutic effects can be achieved.
Research on antibacterial drugs
As an intermediate in lysine metabolism, its metabolic pathway is a precursor to the synthesis of various antibiotics, such as bacteriocins. By regulating its metabolism, the biosynthetic efficiency of antibiotics can be enhanced, providing new ideas for the development of antibacterial drugs. Researchers use gene editing technology to regulate key enzymes in the DCIP metabolic pathway, such as lysine decarboxylase and piperidine reductase, thereby increasing antibiotic production.
Based on the structural characteristics of product, researchers have designed multiple novel antibacterial agents. These antibacterial agents exert their antibacterial effects by interfering with bacterial cell wall synthesis or protein synthesis. With the in-depth study of the metabolic pathway of product, it is expected that more new antibiotics based on its metabolic pathway will be developed in the future, providing more choices for clinical treatment.
Treatment of metabolic diseases
Its metabolic abnormalities are closely related to the occurrence and development of various metabolic diseases. For example, in phenylketonuria, patients have elevated levels of DCIP in their bodies, leading to neurological damage. Researchers have developed various treatment strategies for metabolic diseases caused by abnormal metabolism of DCIP
For example, supplementing with vitamin B6 can promote the metabolism of DCIP, reduce its concentration in the body, and alleviate disease symptoms. In addition, inhibitors or activators targeting specific metabolic enzymes can also be used to regulate the metabolic pathway of DCIP. In the treatment of phenylketonuria, limiting the intake of phenylalanine and supplementing with vitamin B6 can significantly reduce the level of DCIP and improve the metabolic status of patients.
Agricultural Applications: Regulation of Plant Growth and Stress Resistance
Plant physiological functions
It is a key intermediate in lysine metabolism in plants, and its content is regulated by various factors, including environmental stress, nutritional status, and plant development stage. Research has shown that DCIP is involved in nitrogen metabolism pathways in plants and is closely related to the synthesis of amino acids, proteins, and nucleic acids. In addition, as a precursor of secondary metabolites, it participates in the synthesis of plant defense substances such as lignin and flavonoids.
It has signaling molecular functions within the plant body, participating in the regulation of plant growth, development, and stress response. For example, in systemic acquired resistance (SAR), DCIP serves as a key signaling molecule that induces broad-spectrum resistance in plants through the MPK3/6-WRKY33-ALD1-Pipecolic acid regulatory loop. In addition, it also participates in regulating plant hormone signaling pathways, such as synergizing with signaling molecules such as jasmonic acid (JA) and salicylic acid (SA), to enhance plant tolerance to biotic and abiotic stress.
As a biological stimulant, it can promote plant growth, improve nutrient absorption efficiency, and enhance stress resistance. It regulates plant metabolic pathways, optimizes energy allocation, and enables plants to maintain normal physiological functions under adverse conditions. For example, exogenous application of D-Pipecolic Acid can promote root development, enhance photosynthesis, and increase antioxidant enzyme activity, thereby improving overall plant stress resistance.
Application in Plant Growth Regulation
The root system is the main organ for plants to absorb water and nutrients, and its development directly affects plant growth and stress resistance. Research has shown that it can promote root tip cell division and increase root hair density, thereby enhancing root absorption capacity. For example, in soybean seed treatment, 0.5 mM D-Pipecolic Acid can increase germination rate by 12% and seedling fresh weight by 18%. This effect may be related to its regulation of plant hormone balance, promotion of cell division and elongation. Photosynthesis is the core process of energy metabolism in plants, and its efficiency directly affects plant growth and yield.
D-Pipecolic Acid can enhance plant photosynthesis by increasing Rubisco enzyme activity, promoting chlorophyll synthesis, and optimizing light energy utilization efficiency. For example, foliar spraying of 100 mg/L D-Pipecolic Acid during cucumber flowering can increase single fruit weight by 18% and vitamin C content by 22%. This effect may be related to the regulation of plant carbon and nitrogen metabolism balance and the promotion of assimilate accumulation by D-Pipecolic Acid. Plant hormones play a crucial role in plant growth, development, and stress response.
Application in Enhancing Resilience
Drought is one of the main abiotic stresses that limit plant growth and yield. It can improve plant drought resistance by regulating plant water metabolism, enhancing antioxidant enzyme activity, and promoting the accumulation of osmoregulatory substances. For example, wheat seedlings pre treated with 100 μ M D-Pipecolic Acid showed a 45% increase in survival rate under drought stress.
This effect may be related to its regulation of the ABA signaling pathway, promotion of stomatal closure, and reduction of water evaporation. Salt stress is another important abiotic stress that affects plant growth and yield. D-Pipecolic Acid can improve plant salt tolerance by regulating plant ion balance, enhancing antioxidant enzyme activity, and promoting the accumulation of osmoregulatory substances. For example, rice treated with D-Pipecolic Acid under salt stress showed a 30% increase in biomass and a 40% decrease in Na+accumulation. This effect may be related to its regulation of Na+/K+transporters, promotion of Na+efflux, and K+absorption.
Application in Enhancing Resilience
Low temperature stress can damage the structure and function of plant cell membranes, affecting plant growth and yield. It can improve plant cold resistance by regulating the composition of plant membrane lipids, enhancing antioxidant enzyme activity, and promoting the expression of cold resistant genes. For example, tomato seedlings treated with D-Pipecolic Acid showed a 28% decrease in MDA content and reduced damage to the photosynthetic system under low temperature stress.
This effect may be related to its regulation of unsaturated fatty acid synthesis, promotion of cold response protein expression, and enhancement of cell membrane stability. Plant diseases are one of the important factors affecting agricultural production. D-Pipecolic Acid can improve plant disease resistance by regulating plant defense signaling pathways, promoting defense substance synthesis, and enhancing cell wall strength.
For example, it can induce plants to produce defense substances such as disease-related proteins (PR proteins), lignin, and flavonoids, which inhibit the growth and infection of pathogens. In addition, D-Pipecolinic acid can enhance plant systemic acquired resistance (SAR) by regulating plant hormone signaling pathways, such as synergistic effects with SA, JA, etc.
Detailed analysis of molecular structure of D-Pipecolinic acid.
The core structure of D-Pipecolinic acid is a heterocyclic ring containing five atoms, consisting of four carbon atoms and one nitrogen atom, presenting a circular structure similar to that of a Balaka rabbit. The carbon atoms and nitrogen atoms in this heterocyclic ring are arranged in sequence by number, with different functional groups on the carbon atoms.
-Carboxyl group: The D-Pipecolinic acid molecule has a carboxyl group (- COOH) located on the first carbon atom of the heterocyclic structure. The carboxyl group is formed by a carbonyl group (C=O) and an oxygen atom, which is connected with the carbon atom through Covalent bond.
-Amino group: In the D-Pipecolinic acid molecule, there is also an amino group (- NH2) located on the third carbon atom of the heterocyclic structure. The amino group is composed of one nitrogen atom and three hydrogen atoms. The nitrogen atom is connected with the carbon atom through Covalent bond.
-Trans Alkyl group: The second carbon atom in a D-Pipecolinic acid molecule is connected to a cis alkyl group, where two adjacent carbon atoms are connected by sharing a carbon carbon single bond. This cis alkyl group can be different functional groups, such as methyl (CH3) or ethyl (C2H5).
The carbon atom and nitrogen atom in the heterocyclic structure of D-Pipecolinic acid are both planar configurations, that is, their Chemical bond are on the same plane. In addition, the cis alkyl group in the D-Pipecolinic acid molecule is located on one side of the heterocyclic plane.
D-Pipecolinic acid is an acidic compound that can release protons (H+) from carboxyl groups. It plays an important physiological function in organisms, such as being a precursor of an alkaloid and participating in protein synthesis, metabolism, and decomposition processes. In addition, it may have other potential pharmacological and biological effects.
FAQ
What is pipecolic acid?
Pipecolic acid is a piperidinemonocarboxylic acid in which the carboxy group is located at position C-2. It is a conjugate acid of a pipecolate. ChEBI. Pipecolic acid is a metabolite found in or produced by Escherichia coli (strain K12, MG1655).
What is a pipecolic acid blood test?
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.
What is the role of pipecolic acid in plants?
Pipecolic acid (Pip) is a naturally occurring non-protein amino acid, that builds up in plants in response to pathogen infection. Pip is upregulated in autophagy mutants, indicating its role as a crucial regulator of plant immunity by upregulating systemic acquired resistance (SAR).
Is pipecolic acid an organic acid?
Pipecolic acid (piperidine-2-carboxylic acid) is an organic compound with the formula HNC5H9CO2H. It is a carboxylic acid derivative of piperidine and, as such, an amino acid, although one not encoded genetically.
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