54-47-7 Usage
Description
Pyridoxal phosphate is an organic compound formed by the combination of vitamin B6 and phosphoric acid, including pyridoxal, pyridoxamine, and pyridoxine, which exist in the form of phosphate esters in the body. Among them, pyridoxal phosphate and pyridoxamine phosphate can be converted into each other, and they are all active types. Pyridoxal phosphate is the active form of vitamin B6. Several reactions catalyzed by pyridoxal phosphate are: transamination, α-decarboxylation, β-decarboxylation, β-elimination, γ-elimination, racemization and aldol reaction.
Chemical Properties
Light yellow crystalline
Uses
Vitamin (enzyme co-factor).
Definition
The coenzyme of amino acid metabolism that also
is the active group of various decarboxylases and
other types of enzymes. It is closely related to
pyridoxine.
Biological Functions
Pyridoxal phosphate is the coenzyme form of vitamin B6. In the catalytic reaction, the intramolecular aldehyde group of pyridoxal phosphate is combined with the amino group of α-amino acid to form an aldimine, also known as Schiffbase, and then the amino acid undergoes transamination, decarboxylation or racemization according to the characteristics of different enzymes and proteins. . As a coenzyme of amino acid transaminase, decarboxylase and racemase, it plays a very important role in amino acid metabolism.
Synthesis Reference(s)
Journal of the American Chemical Society, 73, p. 4693, 1951 DOI: 10.1021/ja01154a062
Purification Methods
PLP has been purified by dissolving 2g in H2O (10-15mL, in a dialysis bag a third full) and dialysing with gentle stirring against 1L of H2O (+ two drops of toluene) for 15hours in a cold room. The dialysate is evaporated to 80-100mL, then lyophilised. Lemon yellow microscopic needles of the monohydrate remain when all the ice crystals have been removed. The purity is checked by paper chromatography (in EtOH or n-PrOH/NH3) and the spot(s) visualised under UV light after reaction with a spray of p-phenylene diamine, NH3 and molybdate. Solutions stored in a freezer are 2-3% hydrolysed in 3weeks. At 25o, only 4-6% hydrolysis occurs even in N NaOH or HCl, and 2% is hydrolysed at 37o in 1day-but is complete at 100o in 4hours. It is best stored as a dry solid at -20o. In aqueous acid the solution is colourless but is yellow in alkaline solutions. It has UV max at 305nm ( 1100) and 380nm ( 6550) in 0.1 N NaOH; 330nm ( 2450) and 388nm ( 4,900) in 0.05M phosphate buffer pH 7.0 and 295nm ( 6700) in 0.1N HCl. [Peterson et al. Biochemical Preparations 3 34, 119 1953.] The oxime decomposes at 229-230o and is practically insoluble in H2O, EtOH and Et2O. The O-methyloxime decomposes at 212-213o. [Heyl et al. J Am Chem Soc 73 3430 1951.] It has also been purified by column chromatography through Amberlite IRC-50 (H+) [Peterson & Sober J Am Chem Soc 76 169 1954]. [Beilstein 21/13 V 46.]
Check Digit Verification of cas no
The CAS Registry Mumber 54-47-7 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 5 and 4 respectively; the second part has 2 digits, 4 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 54-47:
(4*5)+(3*4)+(2*4)+(1*7)=47
47 % 10 = 7
So 54-47-7 is a valid CAS Registry Number.
54-47-7Relevant articles and documents
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Viscontini et al.
, p. 1834,1839 (1951)
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Thermodynamics and Kinetics of the Reaction between Pyridoxal-5-Phosphate and Hydrazides of 2-Methylfuran-3-Carboxylic and Thiophene-3-Carboxylic Acids in an Aqueous Solution
Gamov,Zavalishin,Kabirov,Usacheva,Sharnin
, p. 192 - 197 (2019/06/03)
Abstract: The stability constants of pyridoxal-5-phosphate hydrazones formed with 2-methylfuran-3-carbohydrazide and thiophene-3-carbohydrazide in an aqueous solution at pH 1.9, 6.6, 7.0, and 7.4 are determined via spectrophotometry. The kinetics of the processes of formation and hydrolysis of the Schiff bases are studied, and the constant of the direct and reverse reactions are calculated from the electronic absorption spectra. The stability constants of the Schiff bases are calculated from their ratio. The thermodynamic parameters of the reaction of formation (log K, ΔH, and TΔS) of both hydrazones at pH 6.6 are determined via calorimetry. The reasons for the differences between the equilibrium constants calculated from the data of spectrophotometric and kinetic experiments are discussed, and the reliability of the obtained results is analyzed.
Method for synthesizing pyridoxal phosphate
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Paragraph 0019; 0021; 0024; 0027; 0030; 0033; 0036; 0039, (2019/01/08)
The present invention discloses a method for synthesizing pyridoxal phosphate (5'-pyridoxal phosphate). According to the method, pyridoxine hydrochloride is used as a starting material, and is oxidized under mild reaction conditions to obtain a pyridoxal acidic salt, and a phosphate esterification reaction is carried out with a phosphate esterification reagent to obtain pyridoxal phosphate. According to the present invention, the method has advantages of easily-available raw materials, simple route, low toxicity, less side-reaction, easy product separation, easy product characterizing, high yield and the like.
