P9255

Pyridoxal 5′-phosphate hydrate

≥98%

• Synonym(s): Pyridoxal phosphate, 3-Hydroxy-2-methyl-5-([phosphonooxy]methyl)-4-pyridinecarboxaldehyde, Codecarboxylase, PLP, Pyridoxal 5-phosphate
• Empirical Formula (Hill Notation): C₈H₁₀NO₆P · xH₂O
• CAS Number: 853645-22-4
• Molecular Weight: 247.14 (anhydrous basis)
• UNSPSC Code: 12352205
• NACRES: NA.79
• PubChem Substance ID: 24899020
• EC Number: 200-208-3
• Beilstein/REAXYS Number: 234749
• MDL number: MFCD00006333

Properties

• biological source: synthetic (organic)
• Quality Level: 200
• assay: ≥98%
• form: powder
• technique(s): HPLC: suitable
• color: beige, off-white to yellow
• mp: 140-143 °C
• storage temp.: −20°C
• SMILES string: CC1=NC=C(COP(O)(O)=O)C(C([H])=O)=C1O
• InChI: 1S/C8H10NO6P/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)
• InChI key: NGVDGCNFYWLIFO-UHFFFAOYSA-N

Description

General description

Pyridoxal 5′-phosphate (PLP) is synthesized in a multiple-step process. The two pathways inlcude pyridoxal phosphate biosynthetic protein (PdxA)- pyridoxine-5′-phosphate synthase (PdxJ) pathway and the pyridoxal 5′-phosphate synthase subunit PDX1/PDX2 pathway. It is the active form of pyridoxine.

Application

Pyridoxal 5′-phosphate hydrate has also been used:

• as a reference standard to quantify vitamin B₆ in feed and digesta samples using high performance liquid chromatography (HPLC)
• in D-amino acid transaminase reaction(10)
• as a cofactor for L-glutamic acid decarboxylase

Biochem/physiol Actions

Pyridoxal 5′-phosphate (PLP) aids in carbohydrate and fat metabolism by serving as a cofactor. It is majorly responsible for catalyzing the enzymatic reactions involved in sphingolipid synthesis and neurotransmitter (dopamine and serotonin) synthesis. PLP is used in the studies of PLP-dependent enzyme active sites. PLP is also a cofactor for a wide range of enzymes including mitochondrial 5-Aminolevulinic acid synthase (ALAS) cysteine desulfurase, cystathionine γ-synthase (CGS), ornithine 4,5-aminomutase (OAM),[1] and D-serine dehydratase.

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Gloves, type N95 (US)