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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:
Molecular Weight:
248.17
Beilstein:
233653
EC Number:
MDL number:
UNSPSC Code:
12352116
PubChem Substance ID:
NACRES:
NA.79

Quality Level

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

Signal Word

Warning

Hazard Statements

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

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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Sonia Herrero et al.
Plant molecular biology, 76(1-2), 157-169 (2011-05-03)
Vitamin B6 (pyridoxal phosphate) is an essential cofactor in enzymatic reactions involved in numerous cellular processes and also plays a role in oxidative stress responses. In plants, the pathway for de novo synthesis of pyridoxal phosphate has been well characterized
I Miyahara et al.
Journal of biochemistry, 116(5), 1001-1012 (1994-11-01)
The three-dimensional structures of pyridoxamine 5'-phosphate-type aspartate aminotransferase from Escherichia coli and its complexes with maleate and glutarate have been determined by X-ray crystallography at 2.2, 2.1, and 2.7 A resolution, respectively. The enzyme is a dimeric form comprising two
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
Identification of a pyridoxine (pyridoxamine) 5'-phosphate oxidase from Arabidopsis thaliana.
Sang Y, Barbosa JM, Wu H, Locy RD, Singh NK.
Febs Letters, 2007, 344-348 (2007)
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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