Pyridoxal 5'-phosphate monohydrate

Bezeichnung:Pyridoxal 5'-phosphate monohydrate

CAS-Nr41468-25-1

Englisch Name:Pyridoxal 5'-phosphate monohydrate

CBNumberCB6757175

SummenformelC8H12NO7P

Molgewicht265.16

MOL-Datei41468-25-1.mol

Pyridoxal 5'-phosphate monohydrate physikalisch-chemischer Eigenschaften

Schmelzpunkt	140-143 °C(lit.)
storage temp.	2-8°C
Löslichkeit	Acetonitrile (Slightly), DMSO (Slightly)
Aggregatzustand	Crystalline Powder
Farbe	Pale yellow
Wasserlöslichkeit	5 g/L (20 ºC)
Sensitive	Light Sensitive
Merck	14,7979
BRN	234749
Stabilität	Air Sensitive, Moisture Sensitive
InChI	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
InChIKey	CEEQUQSGVRRXQI-UHFFFAOYSA-N
SMILES	C1(COP(=O)(O)O)=CN=C(C)C(O)=C1C=O.O
CAS Datenbank	41468-25-1(CAS DataBase Reference)

Sicherheit

Kennzeichnung gefährlicher	Xi
R-Sätze:	36/37/38
S-Sätze:	24/25-36-26
WGK Germany	2
RTECS-Nr.	UV1208000
F	8-10-23
TSCA	Yes
HS Code	29333990

Gefahreninformationscode (GHS)

Pyridoxal 5'-phosphate monohydrate Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
S-Sätze Betriebsanweisung:
S24/25:Berührung mit den Augen und der Haut vermeiden.
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
Chemische Eigenschaften
Pyridoxal Phosphate Hydrate occurs as a pale yellow-white to light yellow crystalline powder.
It is slightly soluble in water, and practically insoluble in ethanol (99.5).
It dissolves in dilute hydrochloric acid and in sodium hydroxide TS.
The pH of a solution prepared by dissolving 0.1 g of Pyridoxal Phosphate Hydrate in 200 mL of water is between 3.0 and 3.5.
Pyridoxal Phosphate Hydrate is colored to light red by light.
Verwenden
Pyridoxal 5-phosphate (PLP) (active form of Vitamin B6) is an enzyme prosthetic group that acts as a coenzyme in transamination, decarboxylation and deamination reactions such as the conversion of dopa into dopamine; of glutamate into GABA; of histidine to histamine. PLP works mechanistically through formation of a Schiff-base.
Definition
ChEBI: Pyridoxal 5-phosphate monohydrate is a pyridinecarbaldehyde.
Application
Pyridoxal 5′-phosphate (PLP), an active form of vitamin B6/ pyridoxine is the coenzyme of amino acid metabolism.
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.
Biosynthese
Two distinct pathways for Pyridoxal 5′-phosphate (PLP) biosynthesis are known. 1.The 'DXP dependent' pathway is found in Escherichia coli and a few members of the γ subdivision of proteobacteria and has been extensively characterized. In this pathway deoxyxylulose 5-phosphate (DXP) is condensed with 3-hydroxy-1-aminoacetone phosphate to give PNP. PNP is oxidized to PLP by PdxH. The DXP dependent pathway is not widely distributed and is surprisingly complex requiring seven enzymes (GapB, PdxB, PdxF (SerC), PdxA, DXS, PdxJ and PdxH). This pathway was the first discovered and it has been extensively reviewed. 2. The second pathway uses Pdx1 and Pdx2 to catalyze the condensation of d-ribose 5-phosphate (R5P), glutamine and glyceraldehyde 3-phosphate to form PLP. The mechanistic and structural characterization of both pathways is at an advanced stage.
Allgemeine Beschreibung
Pyridoxal 5'-phosphate (PLP, vitamin B6) is an essential cofactor in all living systems. It is one of the most versatile cofactors and participates in transamination, decarboxylation, racemization, Cα-Cβ cleavage and α-β elimination reactions. PLP plays an important role in amino acid and carbohydrate metabolism and has been implicated in singlet oxygen resistance. PLP can be used as a dietary supplement in cases of vitamin B6 deficiency. Reduced levels of PLP in the brain can cause neurological dysfunction. By inhibiting AGE formation and working as a coenzyme in chemical reactions, pyridoxal 5’-phosphate can support healthy nerve, eye, cardiovascular and kidney function.
Biologische Aktivität
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.

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