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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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.
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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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)
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)
Fluorescence properties of pyridoxamine 5-phosphate.
J E Churchich
Biochimica et biophysica acta, 102(1), 280-288 (1965-05-25)
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
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
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