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/REAXYS Number:
234749
MDL number:
PubChem Substance ID:
NACRES:
NA.51
Pricing and availability is not currently available.

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

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

NONH for all modes of transport

WGK Germany

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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)
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)
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...
Nutritional Deficiencies and Syndromes Associated with Alcoholism
Textbook of Clinical Neurology, 897-917 (2007)

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