| Identification | More | [Name]
Pyridoxal phosphate | [CAS]
54-47-7 | [Synonyms]
3-HYDROXY-2-METHYL-5-[(PHOSPHONOOXY)METHYL]-4-PYRIDINECARBOXALDEHYDE
CODECARBOXYLASE
PYRIDOXAL 5'-MONOPHOSPHATE
PYRIDOXAL 5'-PHOSPHATE
PYRIDOXAL 5-PHOSPHATE
PYRIDOXAL-5-PHOSPHORIC ACID
VITAMIN B6
3-hydroxy-2-methyl-5-((phosphonooxy)methyl)-4-pyridinecarboxaldehyd
3-hydroxy-2-methyl-5-[(phosphonooxy)methyl]-4-pyridinecarboxaldehyd
apolonb(sub6)
apolonb6
biosechs
hairoxal
hexerminp
hiadelon
hi-pyridoxin
pal-p
phosphopyridoxal
phosphoridoxalcoenzyme
piodel | [EINECS(EC#)]
200-208-3 | [Molecular Formula]
C8H10NO6P | [MDL Number]
MFCD00006333 | [Molecular Weight]
247.14 | [MOL File]
54-47-7.mol |
| Chemical Properties | Back Directory | [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.
| [Melting point ]
140-143 °C
| [Boiling point ]
565.7±60.0 °C(Predicted) | [density ]
1.638±0.06 g/cm3(Predicted) | [storage temp. ]
−20°C
| [solubility ]
DMSO (Slightly, Heated), Methanol (Slightly), Water (Slightly) | [form ]
powder
| [pka]
1.56±0.10(Predicted) | [Stability:]
Hygroscopic | [InChI]
InChI=1S/C8H10NO6P/c1-5-8(11)7(3-10)6(2-9-5)4-15-16(12,13)14/h2-3,11H,4H2,1H3,(H2,12,13,14) | [InChIKey]
NGVDGCNFYWLIFO-UHFFFAOYSA-N | [SMILES]
C1(C)=NC=C(COP(O)(O)=O)C(C=O)=C1O | [LogP]
-1.921 (est) | [CAS DataBase Reference]
54-47-7(CAS DataBase Reference) | [EPA Substance Registry System]
54-47-7(EPA Substance) |
| Hazard Information | Back Directory | [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). | [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 | [Mechanism of action]
Pyridoxal phosphate(PLP) acts as a coenzyme in all transamination reactions, and in certain decarboxylation, deamination, and racemization reactions of amino acids. The aldehyde group of PLP forms a Schiff-base linkage (internal aldimine) with the ε-amino group of a specific lysine group of the aminotransferase enzyme. The α-amino group of the amino acid substrate displaces the ε-amino group of the active-site lysine residue in a process known as transaldimination. The resulting external aldimine can lose a proton, carbon dioxide, or an amino acid sidechain to become a quinoid intermediate, which in turn can act as a nucleophile in several reaction pathways. | [storage]
Store at -20°C | [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.] |
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