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P9255

Sigma-Aldrich

Pyridoxal 5′-phosphate hydrate

≥98%

Synonym(s):

Pyridoxal phosphate, 3-Hydroxy-2-methyl-5-([phosphonooxy]methyl)-4-pyridinecarboxaldehyde, Codecarboxylase, PLP, Pyridoxal 5-phosphate

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About This Item

Empirical Formula (Hill Notation):
C8H10NO6P · xH2O
CAS Number:
853645-22-4
Molecular Weight:
247.14 (anhydrous basis)
Beilstein:
234749
EC Number:
200-208-3
MDL number:
MFCD00006333
UNSPSC Code:
12352205
PubChem Substance ID:
24899020
NACRES:
NA.79

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

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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

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.

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
Structure of the mitochondrial aminolevulinic acid synthase, a key heme biosynthetic enzyme
Brown BL, et al.
Structure, 26(4), 580-589 (2018)
Functional characterization of the eukaryotic cysteine desulfurase Nfs1p from Saccharomyces cerevisiae
Muhlenhoff U, et al.
Test, 279(35), 36906-36915 (2004)
Preparation, Stimulation and Other Uses of Adult Rat Brain Synaptosomes
Modi J, et al.
Bio-protocol, 7(24) (2017)
Structure of the cystathionine gamma-synthase MetB from Mycobacterium ulcerans
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