Pyridoxal 5'-phosphate monohydrate, molecular formula C8H10NO6P · H2O, molecular weight 265.15, CAS 41468-25-1. It is a slightly yellow or off white crystalline powder, colorless in dilute acid, yellow in alkali, and almost odorless. Slightly soluble in alcohol solvents, soluble in 200 parts of water, insoluble in chloroform, benzene, acetone, and ether. It is easily soluble in dilute acids such as formic acid, aqueous pyridine, and dilute alkaline solutions, forming a colorless liquid. However, in alkaline solution, it will appear yellow. Sensitive to light and air, it will slowly decompose when exposed to light, and remain stable in dark and low-temperature environments. Pyridoxal phosphate (PLP, the main metabolic active form of vitamin B6) is a multifunctional coenzyme involved in the metabolism of amino compounds. The enzymes that use it as a coenzyme factor are called PLP dependent enzymes (PLDES), which play an important role in the metabolism of sugars, fats, and amino acids, mainly in the biosynthesis of amino acids and biomolecules, such as neurotransmitters serotonin, dopamine, adrenaline, norepinephrine, gamma aminobutyric acid (GABA), and histamine.
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Chemical Formula |
C8H12NO7P |
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Exact Mass |
265 |
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Molecular Weight |
265 |
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m/z |
265 (100.0%), 266 (8.7%), 267 (1.4%) |
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Elemental Analysis |
C, 36.24; H, 4.56; N, 5.28; O, 42.24; P, 11.68 |
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PLP is very important. It participates in the activities of more than 140 PLP dependent enzymes, accounting for about 4% of all classification activities. The versatility of PLP comes from its electrophilicity: at the beginning of the reaction, PLP covalently combines with the substrate through the formation of external aldehydes and imines, and then different types of carbon anion reactions. Chemicalbook intermediates can be stabilized by PLP through resonance effect. This function of PLP is also called "electron trap". In addition to the electron absorption effect, since almost all PLP dependent reactions generate cationic and anionic intermediates, the acidic and basic groups that assist in proton transfer are equally important. Pyridoxal 5-phosphate is an organic synthesis intermediate and pharmaceutical intermediate, which can be used as a biochemical reagent in the laboratory organic synthesis process and chemical medicine research and development process.
Pyridoxal 5'-phosphate monohydrate (PLP), as the active form of vitamin B6, has a wide and important range of applications in living organisms. It is not only a key cofactor for various enzymes, but also participates in various biochemical reactions and metabolic processes, playing a crucial role in maintaining human health.
Enzyme cofactors:
5 '- pyridoxal phosphate monohydrate is a cofactor for various enzymes that play a critical role in carbon and nitrogen metabolism. At least 140 enzymes in the human body rely on this substance to exert their catalytic effects. These enzymes are involved in various biochemical reactions such as amino conversion, decarboxylation, glycogen hydrolysis, carbohydrate synthesis, sphingolipid synthesis, amino acid synthesis, and neurotransmitter metabolism.
As a coenzyme, it participates in the metabolic processes of proteins, including the biosynthesis and catabolism of amino acids. Especially, it plays a crucial role in the metabolism of amino acids such as methionine, cysteine, and cysteine.
Promote amino acid metabolism:
5 '- pyridoxal phosphate monohydrate is a coenzyme of transaminase and decarboxylase in amino acid metabolism, which can promote glutamate decarboxylation and enhance the production of gamma aminobutyric acid. Gamma aminobutyric acid is an important neurotransmitter that plays a crucial role in maintaining the normal function of the nervous system.
It is also a coenzyme involved in the metabolism of citrulline and ornithine, and is involved in the conversion and metabolism of these amino acids.
Stable amino acids:
5 '- pyridoxal phosphate monohydrate can stabilize amino acids and prevent their degradation and loss in non enzymatic reactions in the body. This is of great significance for maintaining the balance and stability of amino acids in the body.
Treatment related diseases:
Due to its important role in amino acid metabolism, 5'- pyridoxale phosphate monohydrate is clinically used to treat diseases associated with amino acid metabolism disorders. For example, it can be used to treat diseases caused by abnormal amino acid metabolism, such as hyperoxaluria and gout.
In neurological disorders such as epilepsy and seizures, 5'- pyridoxale phosphate monohydrate, as a coenzyme for the synthesis of gamma aminobutyric acid and serotonin, can reduce neural excitability and alleviate related symptoms.
In addition, it is also used to treat neurodegenerative diseases such as Parkinson's disease, improving patients' symptoms by increasing dopamine levels in the body.
Adjuvant therapy:
In the treatment of cardiovascular diseases, 5 '- pyridoxale phosphate monohydrate can be used as an adjuvant therapy drug to help regulate blood lipid metabolism, lower blood pressure, and more.
It can also be used to alleviate pregnancy symptoms such as nausea and vomiting.
5 '- pyridoxale phosphate monohydrate also plays a role in maintaining immune system function.
Biological Manufacturing and Tissue Engineering:
In the fields of biomanufacturing and tissue engineering, 5 '- pyridoxal phosphate monohydrate serves as an important supplement to serum-free culture media, promoting cell growth, metabolism, and differentiation. Adding an appropriate amount of this substance can significantly improve the cell growth environment, enhance culture efficiency, and improve product quality. This is of great significance for fields such as cell therapy, tissue repair, and regenerative medicine.
Cell culture:
During cell culture, 5 '- pyridoxale phosphate monohydrate is widely used to improve cell growth conditions. It can stimulate the production of lipids and neurotransmitters, providing necessary nutrients and growth factors for cells. This plays an important role in cell proliferation, differentiation, and functional expression.
Drug synthesis:
As a key intermediate in drug synthesis, 5 '- pyridoxale phosphate monohydrate plays an important role in the preparation of various drugs. It participates in regulating the mechanism of action of drugs related to amino acid metabolism disorders, improving the efficacy and safety of drugs. In addition, it can also be used to synthesize other biologically active compounds, further expanding its application fields.
Biochemical reaction research:
In the field of scientific research, Pyridoxal 5'-phosphate monohydrate is widely used in the study of various biochemical reactions. It participates in various physiological processes such as fatty acid metabolism, neurotransmitter synthesis, and immune function regulation as a coenzyme of multiple enzymes. By delving into its mechanism of action and potential applications, researchers can better understand the regulatory mechanisms of related metabolic pathways, providing new ideas and methods for disease treatment.
Pyridoxal phosphate is an important bioactive substance that participates in various biochemical reactions in organisms as the active form of vitamin B6
Reaction principle:
This step utilizes active manganese dioxide (MnO ₂) as an oxidant to oxidize pyridoxine HCl (the hydrochloride salt of vitamin B6) to pyridoxale HCl. This is a typical oxidation reaction, in which manganese dioxide acts as a mild oxidant and can selectively oxidize alcohol groups to aldehyde groups.
Operation steps:
Dissolve an appropriate amount of pyridoxine hydrochloride in a suitable solvent (such as ethanol or water) to ensure complete dissolution.
Add an appropriate amount of active manganese dioxide powder and stir evenly.
Stir the reaction mixture under mild conditions (such as room temperature or slight heating) until the reaction is complete (reaction progress can be monitored by TLC or HPLC).
Filter out the manganese dioxide catalyst and wash the filter cake with solvent to recover the residual product.
Concentrate and purify the filtrate to obtain PL HCL.
Reaction principle:
This step connects PL HCL with N, N-dimethylethylenediamine (DMEDA) through a condensation reaction to form a 3-Hydroxy-5-(hydroxymethyl)-2-methylisonicotinaldehyde condensate. This is a typical amine aldehyde condensation reaction, usually carried out under acidic conditions to promote nucleophilic addition of amines to aldehydes.
Operation steps:
Dissolve PL HCL in a suitable solvent (such as ethanol or methanol).
Add an appropriate amount of N, N-dimethylethylenediamine and a small amount of acid (such as acetic acid) to catalyze the reaction.
Stir the reaction mixture at room temperature or slightly heated until the reaction is complete (also monitored by TLC or HPLC).
Post treatment of the reaction mixture, such as concentration, crystallization, or extraction, to separate and purify pyridoxale condensates.
Reaction principle:
This step converts pyridoxale condensate into pyridoxale phosphate through phosphorylation reaction. Polyphosphate (such as sodium pyrophosphate or sodium tripolyphosphate) is used as a phosphorylation reagent to react with 3-Hydroxy-5-(hydroxymethyl)-2-methylisonicotinaldehyde condensate under appropriate conditions to produce the target product.
Operation steps:
Dissolve the pyridoxale condensate in a suitable solvent (such as DMSO or DMF).
Add an appropriate amount of polyphosphate and adjust the pH of the reaction system to a suitable range (usually alkaline).
Stir the reaction mixture under heating conditions (such as 60-80 ° C) until the reaction is complete.
Post treatment of the reaction mixture, such as neutralization, concentration, crystallization, or extraction, to separate and purify crude pyridoxale phosphate.
The above is a synthesis method of pyridoxale phosphate, which gradually constructs the target product through three steps: oxidation, condensation, and phosphorylation. In practical operation, it is necessary to adjust and optimize the reaction conditions appropriately according to laboratory conditions and raw material quality. In addition, sufficient post-treatment and purification work is required after each reaction step to ensure the quality and purity of the final product.
FAQ
What is pyridoxal 5-phosphate monohydrate used for?
Pyridoxal phosphate is a vitamin available in many formulations to correct vitamin B6 deficiency. This is the active form of vitamin B6 serving as a coenzyme for synthesis of amino acids, neurotransmitters (serotonin, norepinephrine), sphingolipids, aminolevulinic acid.
Is P5P the same as B6?
Pyridoxal phosphate (PLP, pyridoxal 5'-phosphate, P5P), the active form of vitamin B6, is a coenzyme in a variety of enzymatic reactions.
What does the P5P supplement do?
Thorne Pyridoxal 5'-Phosphate is necessary for homocysteine recycling and the production of hemoglobin and intrinsic factor. If your body has trouble converting pyridoxine to P5P, supplementing this ensure the most bioactive form of vitamin B6 is being supplemented.
What are the benefits of taking pyridoxal phosphate?
Pyridoxal 5′-phosphate (the active form of vitamin B6) is a necessary cofactor for the formation of several important neurotransmitters associated with stress. Within the brain, glutamic acid is converted to GABA via the enzyme glutamate decarboxylase and its cofactor pyridoxal 5′-phosphate.
What happens if I take B6 every day?
Taking 200mg or more a day of vitamin B6 can lead to a loss of feeling in the arms and legs known as peripheral neuropathy. This will usually improve once you stop taking the supplements.
Is pyridoxal phosphate the same as vitamin B6?
Pyridoxal 5' phosphate (PLP) and pyridoxamine 5' phosphate (PMP) are the active coenzyme forms of vitamin B6. Substantial proportions of the naturally occurring pyridoxine in fruits, vegetables, and grains exist in glycosylated forms that exhibit reduced bioavailability.
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