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82890

Sigma-Aldrich

Pyridoxamine-5′-phosphate

≥98.0% (HPLC)

Synonym(s):

4-Aminomethyl-5-hydroxy-6-methyl-3-pyridylmethyl phosphate

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About This Item

Empirical Formula (Hill Notation):
C8H13N2O5P
CAS Number:
529-96-4
Molecular Weight:
248.17
Beilstein:
233653
EC Number:
208-471-6
MDL number:
MFCD00023504
UNSPSC Code:
12352116
PubChem Substance ID:
57652936
NACRES:
NA.79

Assay

≥98.0% (HPLC)

form

powder

technique(s)

HPLC: suitable

color

faint beige to light beige
 white to light yellow

SMILES string

Cc1ncc(COP(O)(O)=O)c(CN)c1O

InChI

1S/C8H13N2O5P/c1-5-8(11)7(2-9)6(3-10-5)4-15-16(12,13)14/h3,11H,2,4,9H2,1H3,(H2,12,13,14)

InChI key

ZMJGSOSNSPKHNH-UHFFFAOYSA-N

General description

Pyridoxamine is a derivative of vitamin B6. Pyridoxamine is a water-soluble vitamin. Vitamin B6 derivatives contain a core pyridine ring. Pyridoxaminecontains an amino methyl group at pyridine′s 4′ position.

Application

Pyridoxamine-5′-phosphate is suitable:
  • in the enzymatic synthesis of cytidine diphosphate-4-keto-3, 6-dideoxyglucose
  • as a substrate for pyridoxamine-5′-phosphate phosphatase activity assay
  • as a substrate to characterize pyridoxine-5′-phosphate oxidase
  • for the absorbance and fluorescence studies of properties of NaBH4-reduced glycogen phosphorylase b to probe the microenvironment of PMP residue
  • as a substrate for characterization of pyridoxamine-phosphate transaminase(s) from various species and tissues

Biochem/physiol Actions

Pyridoxal 5′-phosphate can be converted to pyridoxamine-5′-phosphate in the presence of (S)-α-methylbenzylamine (MBA) as the amine donor by using pyruvate transaminase as a biocatalyst. Pyridoxine 5′-phosphate and pyridoxamine 5′-phosphate are oxidized to pyridoxal 5′-phosphate (PLP) using flavin mononucleotide (FMN) as the immediate electron acceptor and oxygen as the ultimate electron acceptor by the E. coli enzyme pyridoxine (pyridoxamine) 5′-phosphate oxidase.
pK of pyridoxamine-5′-phosphate (pyridoxamine 5-phosphate, PAMP) in the singlet excited state has been evaluated by absorption and fluorescence spectral studies.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

82890-BULK:
82890-10MG:
82890-VAR:
82890-50MG:

Certificates of Analysis (COA)

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L Lumeng et al.
The Journal of biological chemistry, 250(20), 8126-8131 (1975-10-25)
The tissue content of pyridoxal 5'-phosphate is controlled principally by the protein binding of this coenzyme and its hydrolysis by a cellular phosphatase. The present study identifies this enzyme and its intracellular location in rat liver. Pyridoxal-P is not hydrolyzed
J D Choi et al.
The Journal of biological chemistry, 258(2), 840-845 (1983-01-25)
The kinetic properties of pyridoxamine (pyridoxine)-5'-phosphate oxidase have been studied using the physiological substrates pyridoxine 5'-phosphate (PNP) and pyridoxamine 5'-phosphate (PMP) at 25 degrees C and pH 8.0. Under steady-state conditions with different concentrations of PNP and O2, a series
E S Yang et al.
Archives of biochemistry and biophysics, 377(1), 109-114 (2000-04-25)
Escherichia coli pyridoxine (pyridoxamine) 5'-phosphate oxidase (PNPOx) catalyzes the oxidation of pyridoxine 5'-phosphate and pyridoxamine 5'-phosphate to pyridoxal 5'-phosphate (PLP) using flavin mononucleotide (FMN) as the immediate electron acceptor and oxygen as the ultimate electron acceptor. This reaction serves as
On the microenvironment of the pyridoxamine 5-phosphate residue in NaBH 4 -reduced glycogen phosphorylase b. Absorption and fluorescence studies.
M Cortijo et al.
European journal of biochemistry, 29(1), 134-142 (1972-08-18)
Synthesis of pyridoxamine 5?-phosphate using an MBA: pyruvate transaminase as biocatalyst.
Schell U, et al.
Journal of Molecular Catalysis. B, Enzymatic, 59, 279-285 (2009)
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