P7252

Sigma-Aldrich

Phospho(enol)pyruvic acid tri(cyclohexylammonium) salt

≥98% (enzymatic)

Synonym(s):
PEP-3CHA, 2-(Phosphonooxy)-2-propenoic acid tri(cyclohexylammonium) salt, Phosphoenolpyruvic acid tris(cyclohexylamine) salt
Empirical Formula (Hill Notation):
C3H5O6P · 3C6H13N
CAS Number:
Molecular Weight:
465.56
Beilstein/REAXYS Number:
3752336
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.83

Quality Level

assay

≥98% (enzymatic)

form

powder

solubility

water: 100 mg/mL, clear to very slightly hazy, colorless to faintly yellow

storage temp.

−20°C

SMILES string

NC1CCCCC1.NC2CCCCC2.NC3CCCCC3.OC(=O)C(=C)OP(O)(O)=O

InChI

1S/3C6H13N.C3H5O6P/c3*7-6-4-2-1-3-5-6;1-2(3(4)5)9-10(6,7)8/h3*6H,1-5,7H2;1H2,(H,4,5)(H2,6,7,8)

InChI key

MJKYGUXBFYGLLM-UHFFFAOYSA-N

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General description

Phospho(enol)pyruvic acid is a highly functionalized small molecule. It plays a major role in the metabolism.

Application

Phospho(enol)pyruvic acid tri(cyclohexylammonium) salt has been used:
  • in the pyruvate kinase/lactate dehydrogenase enzyme kinetic assay
  • in the reaction mixture to determine fructokinase activity of Zobellia galactanivorans
  • in luminometry to determine the amount of ADP formed by measuring the increase in light output

Biochem/physiol Actions

Phospho(enol)pyruvic acid is significant in high-phosphate group-transfer function. PEP plays a major role in PEP:sugar phosphotransferase system (PTS) mediated phosphorylation and transport of carbohydrates across the bacterial membrane. It functions to generate natural phosphonates catalyzed by PEP mutase. It plays a key role in the peptidoglycan cell wall biosynthesis.
Phospho(enol)pyruvic acid (PEP) is involved in glycolysis and gluconeogenesis. In glycolysis, PEP is metabolized by pyruvate kinase to yield pyruvate. In plants, PEP is involved in the formation of aromatic amino acids as well as in the carbon fixation pathway.

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis
Certificate of Origin
Determination of Fructokinase Activity from Zobellia galactanivorans
Groisillier A and Tonon T
Bio-protocol, 5(21), e1633-e1633 (2015)
Secretion from dense granules
Methods in Molecular biology: Platelets and Megakaryocytes, volume 1, functional assays, 89-91 (2004)
Synthesis of phosphoenol pyruvate (PEP) analogues and evaluation as inhibitors of PEP-utilizing enzymes
Garcia-Alles LF and Erni B
European Journal of Biochemistry, 269(13), 3226-3236 (2002)
Structural basis for kinase-mediated macrolide antibiotic resistance
Fong DH, et al.
Structure, 25(5), 750-761 (2017)
Jan Niemann et al.
Free radical biology & medicine, 102, 174-187 (2016-11-29)
Mitochondrial dysfunction affects liver metabolism, but it remains unclear whether this interferes with normal liver aging. We investigated several mitochondrial pathways in hepatocytes and liver tissue from a conplastic mouse strain compared with the control C57BL/6NTac strain over 18 months...

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