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82870 Sigma-Aldrich

Pyridoxal 5′-phosphate monohydrate

≥97.0% (NT)

Synonym: 3-Hydroxy-2-methyl-5-([phosphonooxy]methyl)-4-pyridinecarboxaldehyde, Codecarboxylase, P5P, PLP, Pyridoxal 5-phosphate

  • CAS Number 41468-25-1

  • Empirical Formula (Hill Notation) C8H10NO6P · H2O

  • Molecular Weight 265.16

  •  Beilstein/REAXYS Number 234749

  •  MDL number MFCD00149414

  •  PubChem Substance ID 57652935

  •  NACRES NA.51

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Properties

Related Categories Aldehydes, Analytical Reagents, Analytical/Chromatography, Biochemicals and Reagents, Building Blocks,
Quality Level   100
biological source   synthetic
assay   ≥97.0% (NT)
form   powder
application(s)   cell analysis: suitable
  enzyme immunoassay: suitable
color   white to light yellow
mp   140-143 °C (lit.)
anion traces   chloride (Cl-): ≤500 mg/kg
  sulfate (SO42-): ≤50 mg/kg
cation traces   Ca: ≤20 mg/kg
  Cd: ≤5 mg/kg
  Co: ≤5 mg/kg
  Cr: ≤5 mg/kg
  Cu: ≤5 mg/kg
  Fe: ≤50 mg/kg
  K: ≤50 mg/kg
  Mg: ≤5 mg/kg
  Mn: ≤5 mg/kg
  Na: ≤2000 mg/kg
  Ni: ≤5 mg/kg
  Pb: ≤5 mg/kg
  Zn: ≤5 mg/kg
storage temp.   2-8°C
SMILES string   [H]O[H].[H]C(=O)c1c(COP(O)(O)=O)cnc(C)c1O
InChI   1S/C8H10NO6P.H2O/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);1H2
InChI key   CEEQUQSGVRRXQI-UHFFFAOYSA-N

Description

General description

Pyridoxal 5′-phosphate (PLP), an active form of vitamin B6/ pyridoxine is the coenzyme of amino acid metabolism.

Application

Pyridoxal 5′-phosphate monohydrate has been used:
• as a component in the reaction mixture for ornithine decarboxylase (ODC) activity assay
• as a standard to quantify the concentration of pyridoxal 5′-phosphate (PLP) in cerebrospinal fluid (CSF) of children
• as a dietary supplement to study its effects on the lethal phenotype of mutant flies

Biochem/physiol Actions

Pyridoxine participates in the production of lipid and neurotransmitters. Pyridoxal 5′-phosphate (PLP) serves as a cofactor to stabilize carbanions at Cα of amino acids. Pyridoxine deficiency results in peripheral neuropathy. Absence of PLP leads to neonatal epileptic encephalopathy. PLP acts as a coenzyme in transamination, decarboxylation and deamination reactions such as the conversion of dopa into dopamine; of glutamate into γ aminobutyric acid (GABA); of histidine to histamine. PLP works mechanistically through formation of a Schiff-base.

Other Notes

Coenzymes and Cofactors, vol. 1: Vitamin B6, Pyridoxal Phosphate

Safety & Documentation

Safety Information

Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
2
RTECS 
UV1208000

Documents

Certificate of Analysis (COA)

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Protocols & Articles
Peer-Reviewed Papers
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References

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