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82890 Sigma-Aldrich

Pyridoxamine-5′-phosphate

≥98.0% (HPLC)

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

  • CAS Number 529-96-4

  • Empirical Formula (Hill Notation) C8H13N2O5P

  • Molecular Weight 248.17

  •  Beilstein/REAXYS Number 233653

  •  EC Number 208-471-6

  •  MDL number MFCD00023504

  •  PubChem Substance ID 57652936

  •  NACRES NA.79

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Properties

Related Categories Biochemicals and Reagents, Vitamin B, Vitamin B6, Vitamins
Quality Level   100
assay   ≥98.0% (HPLC)
form   powder
application(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

Description

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.

Other Notes

Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. 82890.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Safety & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Hazard statements 
Precautionary statements 
Target organs 
Respiratory system
Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 2
RTECS 
UT4710000
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Protocols & Articles
Peer-Reviewed Papers
15

References

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