82890
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
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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.
Signal Word
Warning
Hazard Statements
Precautionary 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)
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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)
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)
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
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