P9255

Sigma-Aldrich

Pyridoxal 5′-phosphate hydrate

≥98%

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

Quality Level

biological source

synthetic (organic)

assay

≥98%

form

powder

application(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

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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

Packaging

1, 5, 25 g in poly bottle

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), and D-serine dehydratase.

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

A catalytic mechanism that explains a low catalytic activity of serine dehydratase like-1 from human cancer cells: crystal structure and site-directed mutagenesis studies
Yamada T, et al.
Biochim. Biophys. Acta Gen. Subj., 1780(5), 809-818 (2008)
Functional characterization of the eukaryotic cysteine desulfurase Nfs1p from Saccharomyces cerevisiae
Muhlenhoff U, et al.
Test, 279(35), 36906-36915 (2004)
Structure of the mitochondrial aminolevulinic acid synthase, a key heme biosynthetic enzyme
Brown BL, et al.
Structure, 26(4), 580-589 (2018)
Physical and enzymological interaction of Bacillus subtilis proteins required for de novo pyridoxal 5?-phosphate biosynthesis
Belitsky BR
Journal of Bacteriology, 186(4), 1191-1196 (2004)
Structure of the cystathionine gamma-synthase MetB from Mycobacterium ulcerans
Clifton MC, et al.
Acta Crystallographica. Section F, Structural Biology Communications, 67(9), 1154-1158 (2011)

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