| Identification | Back Directory | [Name]
3-Hydroxy-2-methyl-5-([phosphonooxy]methyl)-4-pyridinecarboxaldehyde | [CAS]
853645-22-4 | [Synonyms]
Pyridoxal 5&rsquo
-phosphate (hydrate)
3-Hydroxy-2-methyl-5
PYRIDOXAL-5-PHOSPHATE
Pyridoxaol-5-phosphate
PYRIDOXAL-5'-PHOSPHATE
Pyridoxal-[d3] Phosphate
PYRIDOXAL 5'-PHOSPHATE HYDRATE POWDE
PYRIDOXAL 5'-PHOSPHATE HYDRATE, >=98
Pyridoxal-[d3] Phosphate(Vitamin B6-[d3])
Pyridoxal 5’-Phosphate ISO 9001：2015 REACH
5-(Phosphonooxy)-3-hydroxy-2-methylpyridine-4-carbaldehyde
Phosphoric acid 2-methyl-3-hydroxy-4-formylpyridine-5-yl ester
(4-formyl-5-hydroxy-6-methyl-3-pyridinyl)methyl dihydrogen phosphate
(4-ForMyl-5-hydroxy-6-Methylpyridin-3-yl)Methyl dihydrogen phosphate
3-Hydroxy-2-methyl-5-([phosphonooxy]methyl)-4-pyridinecarboxaldehyde
3-Hydroxy-2-methyl-5-[(phosphonooxy)methyl]-4-pyridinecarboxaldehyde
Pyridoxal 5'-phosphate hydrate powder, BioReagent, suitable for cell culture
(4-Formyl-5-hydroxy-6-methylpyridin-3-yl)methyl dihydrogen phosphate hydrate(1:x) | [EINECS(EC#)]
200-208-3 | [Molecular Formula]
C8H10NO6P | [MDL Number]
MFCD00006333 | [MOL File]
853645-22-4.mol | [Molecular Weight]
247.14 |
| Chemical Properties | Back Directory | [Melting point ]
140-143 ºC | [storage temp. ]
?20°C | [solubility ]
DMSO (Slightly, Heated), Methanol (Slightly), Water (Slightly) | [form ]
powder | [pka]
pKa 8.69(H2O
t = 25
I = 0.15)(Approximate) | [color ]
White to Pale Yellow | [Odor]
Odorless | [biological source]
synthetic (organic) | [BRN ]
234749 | [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 |
| Hazard Information | Back Directory | [Uses]
Enzyme cofactor.Normal coenzyme form of Vitamin B6 | [Definition]
ChEBI: Pyridoxal 5'-phosphate is the monophosphate ester obtained by condensation of phosphoric acid with the primary hydroxy group of pyridoxal. It has a role as a coenzyme, a human metabolite, an Escherichia coli metabolite, a Saccharomyces cerevisiae metabolite, a mouse metabolite, an EC 2.7.7.7 (DNA-directed DNA polymerase) inhibitor and a cofactor. It is a vitamin B6 phosphate, a member of methylpyridines, a monohydroxypyridine and a pyridinecarbaldehyde. It is functionally related to a pyridoxal. It is a conjugate acid of a pyridoxal 5'-phosphate(2-). | [General Description]
Pyridoxal 5′-phosphate (PLP) is synthesized in a multiple-step process. The two pathways inlcude pyridoxal phosphate biosynthetic protein (PdxA)- pyridoxine-5′-phosphate synthase (PdxJ) pathway and the pyridoxal 5′-phosphate synthase subunit PDX1/PDX2 pathway. It is the active form of pyridoxine. | [Biochem/physiol Actions]
Pyridoxal 5′-phosphate (PLP) aids in carbohydrate and fat metabolism by serving as a cofactor. It is majorly responsible for catalyzing the enzymatic reactions involved in sphingolipid synthesis and neurotransmitter (dopamine and serotonin) synthesis. PLP is used in the studies of PLP-dependent enzyme active sites. PLP is also a cofactor for a wide range of enzymes including mitochondrial 5-Aminolevulinic acid synthase (ALAS) cysteine desulfurase, cystathionine γ-synthase (CGS), ornithine 4,5-aminomutase (OAM), and D-serine dehydratase. | [Biotechnological Applications]
Pyridoxal 5’-Phosphate(PLP) is also often employed as an inhibitor and site-directed, conformationally sensitive reporter group for studying the environment of reactive amino groups within proteins. PLP forms aldimine adducts that can be reduced with nucleophilic reducing reagents such as sodium borohydride or sodium cyanoborohydride. Solid PLP is light-sensitive, and solutions should be prepared fresh. There are four pKa values associated with this coenzyme: a pKa < 2.5 and another at 6.20 for the phosphate group, a pKa of 4.14 for the hydroxyl group, and a pKa of 8.69 for the pyridinium group.
| [Synthesis]
A process for the synthesis ofpyridoxal5' -phosphate, comprising the steps of:
a) adding phenetidine into pyridoxal solution, and reacting to generate pyridoxal Schiff base;
b) adding pyridoxal Schiff base into ionic liquid, and stirring until the pyridoxal Schiff base is fully dissolved to obtain an ion mixed solution; adding pyridoxal Schiff base into ionic liquid, stirring at 35-45 ℃, and cooling the
obtained ionic mixed solution to room temperature after the pyridoxal Schiff base is completely dissolved;
c) adding polyphosphoric acid into the ion mixed solution in which the pyridoxal Schiff base is dissolved, stirring for reaction, cooling after the
reaction is finished, and separating out solids from the ion mixed
solution; filtering solid particles separated out from the ion mixed
solution, wherein the solid obtained by filtering is pyridoxal 5' -phosphate Schiff base, and the obtained liquid is phosphorus-containing ionic liquid; the weight ratio of pyridoxal Schiff base dissolved in the ion mixed solution to the polyphosphoric
acid is within the range of 1:1-1:3, the reaction time is within the
range of 8-12h, the reaction temperature is within the range of 25-40 ℃,
and the temperature is reduced to 10 ℃ after the reaction is finished;
the phosphorus-containing ionic liquid obtained by filtering can be
recycled;
d) carrying out hydrolysis purification reaction on the pyridoxal 5 '-phosphate Schiff base obtained in the step c) to obtain a final product pyridoxal 5' -phosphate. | [Enzyme inhibitor]
This vitamin B6-derived coenzyme (FWfree-acid = 247.14 g/mol; CAS
853645-22-4), often abbreviated PLP, plays a central role in metabolism. In
addition to facilitating aminotransfer reactions, PLP is a coenzyme in
reactions involving: (a) loss of the a-proton, resulting in racemization,
cyclization, or b-elimination/replacement (e.g., alanine racemase, 1-
aminocyclopropane-1-carboxylate synthase, and serine dehydratase,
respectively); (b) loss of the a-carboxylate as carbon dioxide (e.g.,
glutamate decarboxylase); (c) removal/replacement of a group by aldol
cleavage (e.g., threonine aldolase); and (d) catalysis via ketimine
intermediates (e.g., selenocysteine lyase). PLP is also often employed as an
inhibitor and site-directed, conformationally sensitive reporter group for
studying the environment of reactive amino groups within proteins. PLP
forms aldimine adducts that can be reduced with nucleophilic reducing
reagents such as sodium borohydride or sodium cyanoborohydride. Solid
PLP is light-sensitive, and solutions should be prepared fresh. There are
four pKa values associated with this coenzyme: a pKa < 2.5 and another at
6.20 for the phosphate group, a pKa of 4.14 for the hydroxyl group, and a
pKa of 8.69 for the pyridinium group. The coenzyme has an
ultraviolet/visible spectrum: lmax = 330 nm and 388 nm (e = 2500 and 4900
M–1cm–1, respectively) in 50 mM phosphate buffer at pH 7.0; lmax = 305 nm
and 388 nm (e = 1100 and 6550 M–1cm–1, respectively) in 100 mM NaOH.
Pyridoxal 5’-phosphate may also be used as a photosensitizing agent to
modify nearby aminoacyl residues (e.g., histidyl residues in 6-
phosphogluconate dehydrogenase and tryptophanase). Target (s) :
acetylcholinesterase; acetyl-CoA carboxylase; acetyl-CoA
synthetase, or acetate:CoA ligase; N-acetylneuraminate 4-O-
acetyltransferase; acyl-[acyl-carrier-protein]:UDP-N-
acetylglucosamine O-acyltransferase, followed by NaBH4 reduction;
acylphosphatase; adenylate cyclase (6-8); [b-adrenergic-receptor]
kinase; alanine racemase; alcohol dehydrogenase, followed
by NaBH4 reduction; alcohol sulfotransferase (170; aldose reductase
; allantoate deiminase; N- (5-amino-5-carboxypentanoyl) -L-
cysteinyl-D-valine synthetase; 5-aminoleulinate synthase, in the
presence of borohydride; aryl-acylamidase; aspartate
carbamoyltransferase; aspartyl aminopeptidase; ATP-
dependent deoxyribonuclease; BglI restriction endonuclease, type II
site-specific deoxyribonuclease; biliverdin reductase; carbonic
anhydrase, or carbonate dehydratase; casein kinase II;
catechol O-methyltransferase; cathepsin B; cathepsin K
; cathepsin L; cathepsin S; Ca2+-transporting
ATPase; cerebroside sulfotransferase; cholesterol
monooxygenase, side-chain cleaving, or cytochrome P450scc; z-
crystallin/NADPH:quinone oxidoreductase; cytosine deaminase
; dextransucrase; dipeptidyl-peptidase I, or cathepsin
C; DNA-directed DNA polymerase; f29 DNA
polymerase; DNA topoisomerase I; DNA topoisomerase II;
dopa decarboxylase; estrone sulfotransferase;
exodeoxyribonuclease V; F1 ATPase, or H+-transporting two-sector
ATPase; fatty-acid synthase, at enoyl-[acyl-carrier protein] reductase
; fatty-acyl-CoA synthase, yeast, at 3-ketoacyl-[acyl-carrier
protein] reductase step; flavin-containing monooxygenase; b-
fructofuranosidase, or invertase; fructose-1,6-bisphosphate
aldolase; fructose-6-phosphate 2-kinase/fructose-2,6-
bisphosphatase; a1®3 fucosyltransferase; galactosylceramide
sulfotransferase; glucan 1,4-a-glucosidase, or glucoamylase, weakly
inhibited; glucose-6-phosphatase; glucose-1-phosphate
adenylyltransferase; glucose-6-phosphate dehydrogenase; a-
glucosidase; glucuronate reductase; glutamate decarboxylase
; glutamate dehydrogenase; glutathione-disulfide reductase
; glutathione synthetase, slowly inhibited; glyceraldehyde-3-
phosphate dehydrogenase; glycerol-1,2-cyclic-phosphate
phosphodiesterase; glycerol dehydrogenase; glycogen
phosphorylase; glycolipid sulfotransferase; glycoprotein N-
acetylglucosaminyltransferase; glycoprotein 6-a-L-fucosyltransferase
; glycoprotein galactosyltransferase; glycoprotein
sialyltransferase; hemoglobin S polymerization; hexokinase;
HIV (human immunodeficiency virus) reverse transcriptase; H+/K+-
exchanging ATPase; homoserine kinase; H-transporting
ATPase, chloroplast; 2’-hydroxybiphenyl-2-sulfinate desulfinase
; w-hydroxy-fatty-acid:NADP+ oxidoreductase; hydroxyindole-O-
methyltransferase (acetylserotonin O-methyltransferase;
hydroxymethylbilane synthase; 4-hydroxyphenylpyruvate
dioxygenase; inositol-phosphate phosphatase; inositol-3-
phosphate synthase, or inositol-1-phosphate synthase; integrase, HIV
; a-ketoglutarate carrier; a-ketoglutarate dehydrogenase;
kynurenine 3-monooxygenase; lactate dehydrogenase;
lactoylglutathione lyase, or glyoxalase I; malate dehydrogenase;
malate synthase; methanol:5-hydroxybenzimidazolylcobamide Co-
methyltransferase; mevalonate kinase; muri+ne leukemia virus
reverse tr+ans+criptase; myosin ATPase; NAD (P) transhydrogenase
; Na/K-exchanging ATPase; neuraminidase; NMN
nucleosidase, weakly inhibited; nucleoside-diphosphatase;
pancreatic ribonuclease, or ribonuclease A; phenol 2-
monooxygenase; phenol sulfotransferase, or aryl sulfotransferase
; phenylalanyl-tRNA synthetase; phosphoenolpyruvate
carboxylase; phosphofructokinase; phosphogluconate
dehydrogenase; phosphoglucose isomerase; 3-
phosphoglycerate kinase; phospholipase C; phosphomevalonate
kinase; phosphopantothenoylcysteine decarboxylase ; phosphoribulokinase; porphobilinogen synthase, or d-
aminolevulinate dehydratase; pyridoxamine:oxaloacetate
aminotransferase; pyridoxine 4-oxidase; pyruvate
dehydrogenase; pyruvate kinase; pyruvate,orthophosphate
dikinase; retinal oxidase; ribonuclease A;
ribonucleoside-diphosphate reductase; ribosomal proteins
; ribulose-1,5-bisphosphate carboxylase; RNA-directed
DNA polymerase, or reverse transcriptase; RNA polymerase
; serine-sulfate ammonia-lyase; starch phosphorylase;
starch synthase; succinic-semialdehyde dehydrogenase;
thiamin-phosphate pyrophosphorylase; thymidylate synthase
; tissue-specific transcription factor HNF1; tryptophanase
; tryptophan synthase; uracilylalanine synthase;
urocanase; uroporphyrinogen-III synthase; xanthine
dehydrogenase, Drosophila melanogaster. | [storage]
Store at -20°C |
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