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Pyridoxal 5’-Phosphate

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Pyridoxal 5’-Phosphate Basic information

Product Name:
Pyridoxal 5’-Phosphate
Synonyms:
  • Phosphoric acid 2-methyl-3-hydroxy-4-formylpyridine-5-yl ester
  • Pyridoxaol-5-phosphate
  • 3-Hydroxy-2-methyl-5
  • (4-formyl-5-hydroxy-6-methyl-3-pyridinyl)methyl dihydrogen phosphate
  • (4-ForMyl-5-hydroxy-6-Methylpyridin-3-yl)Methyl dihydrogen phosphate
  • PYRIDOXAL 5'-PHOSPHATE HYDRATE POWDE
  • PYRIDOXAL 5'-PHOSPHATE HYDRATE, >=98
  • (4-Formyl-5-hydroxy-6-methylpyridin-3-yl)methyl dihydrogen phosphate hydrate(1:x)
CAS:
853645-22-4
MF:
C8H10NO6P
MW:
247.14
EINECS:
200-208-3
Product Categories:
  • Other Cofactors
  • Vitamin B
  • Vitamin B6
  • Aldehydes
  • and Substrates
  • Biochemicals and Reagents
  • Building Blocks
  • C8
  • Carbonyl Compounds
  • Chemical Synthesis
  • Cofactors
  • Enzymes
  • Inhibitors
  • Nutrition Research
  • Organic Building Blocks
  • Vitamins
Mol File:
853645-22-4.mol
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Pyridoxal 5’-Phosphate Chemical Properties

Melting point:
140-143 ºC
storage temp. 
?20°C
pka
pKa 8.69(H2O t = 25 I = 0.15)(Approximate)
form 
powder
BRN 
234749
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Safety Information

WGK Germany 
3
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Pyridoxal 5’-Phosphate Usage And Synthesis

Uses

Enzyme cofactor.Normal coenzyme form of Vitamin B6

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-Oacetyltransferase; acyl-[acyl-carrier-protein]:UDP-Nacetylglucosamine O-acyltransferase, followed by NaBH4 reduction; acylphosphatase; adenylate cyclase; [b-adrenergic-receptor] kinase; alanine racemase; alcohol dehydrogenase, followed by NaBH4 reduction; alcohol sulfotransferase (170; aldose reductase; allantoate deiminase; N-(5-amino-5-carboxypentanoyl)-Lcysteinyl- D-valine synthetase; 5-aminoleulinate synthase, in the presence of borohydride; aryl-acylamidase; aspartate carbamoyltransferase; aspartyl aminopeptidase; ATPdependent 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; zcrystallin/ 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; bfructofuranosidase, 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; aglucosidase; 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 Nacetylglucosaminyltransferase; 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-Omethyltransferase (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 Comethyltransferase; mevalonate kinase; murine leukemia virus reverse transcriptase; 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 (117,118,153- 155); phosphoribulokinase; porphobilinogen synthase, or daminolevulinate dehydratase; pyridoxamine:oxaloacetate aminotransferase; pyridoxine 4-oxidase; pyruvate dehydrogenase; pyruvate kinase; pyruvate,orthophosphate dikinase (123.124); 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.

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