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Merck

82890

Sigma-Aldrich

Pyridoxamine-5′-phosphate

≥98.0% (HPLC)

Sinónimos:

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

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About This Item

Fórmula empírica (notación de Hill):
C8H13N2O5P
Número de CAS:
Peso molecular:
248.17
Beilstein/REAXYS Number:
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

Categorías relacionadas

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

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves


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Visite la Librería de documentos

Cloning and characterization of a pyridoxine 5'-phosphate oxidase from silkworm, Bombyx mori.
Huang SH, Shi RJ, Zhang JY, Wang Z, Huang LQ.
Insect Biochem., 18, 365-371 (2009)
Enzymatic synthesis of cytidine diphosphate 3,6-dideoxyhexoses. 8. Mechanistic roles of enzyme E-1 and pyridoxamine 5'-phosphate in the formation of cytidine diphosphate-4-keto-3,6-dideoxy-D-glucose from cytidine diphosphate-4-keto-6-deoxy-D-glucose.
P A Rubenstein et al.
The Journal of biological chemistry, 249(12), 3776-3781 (1974-06-25)
Fluorescence properties of pyridoxamine 5-phosphate.
J E Churchich
Biochimica et biophysica acta, 102(1), 280-288 (1965-05-25)
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
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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