82870

Pyridoxal 5′-phosphate monohydrate

≥97.0% (NT)

• Synonym(s): P5P, 3-Hydroxy-2-methyl-5-([phosphonooxy]methyl)-4-pyridinecarboxaldehyde, Codecarboxylase, PLP, Pyridoxal 5-phosphate
• Empirical Formula (Hill Notation): C₈H₁₀NO₆P · H₂O
• CAS Number: 41468-25-1
• Molecular Weight: 265.16
• Beilstein/REAXYS Number: 234749
• MDL number: MFCD00149414
• UNSPSC Code: 12352204
• PubChem Substance ID: 57652935
• NACRES: NA.51

Properties

• biological source: synthetic
• assay: ≥97.0% (NT)
• form: powder
• technique(s): enzyme immunoassay: suitable
• color: white to light yellow
• mp: 140-143 °C (lit.)
• anion traces: chloride (Cl^-): ≤500 mg/kg; sulfate (SO₄^2-): ≤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
• application(s): cell analysis
• storage temp.: 2-8°C
• SMILES string: O=CC1=C(C(C)=NC=C1COP(O)(O)=O)O.[OH]
• 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 Information

• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 2
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Gloves, type N95 (US)