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82870

Sigma-Aldrich

Pyridoxal 5′-phosphate monohydrate

≥97.0% (NT)

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

Quality Level

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

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

Related Categories

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

Storage Class Code

13 - Non Combustible Solids

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificate of Analysis

Certificate of Origin

Regulation and function of pyridoxal phosphate in CNS
Metzler DE
Neurochemistry International, 3(3-4), 207-209 (1981)
Assay of Ornithine Decarboxylase and Spermidine/Spermine N1-acetyltransferase Activities
Hyvonen MT, et al.
Bio-protocol (2014)
Nutritional Deficiencies and Syndromes Associated with Alcoholism
Textbook of Clinical Neurology, 897-917 (2007)
Florence Bourquin et al.
Protein science : a publication of the Protein Society, 20(9), 1492-1508 (2011-06-29)
Sphingolipids are membrane constituents as well as signaling molecules involved in many essential cellular processes. Serine palmitoyltransferase (SPT) and sphingosine-1-phosphate lyase (SPL), both PLP (pyridoxal 5'-phosphate)-dependent enzymes, function as entry and exit gates of the sphingolipid metabolism. SPT catalyzes the...
Vitamin B6 biosynthesis: charting the mechanistic landscape.
Teresa B Fitzpatrick et al.
Chembiochem : a European journal of chemical biology, 11(9), 1185-1193 (2010-04-17)

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