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Merck

P7252

Phospho(enol)pyruvic acid tri(cyclohexylammonium) salt

≥98% (enzymatic), powder

Sinónimos:

2-(Phosphonooxy)-2-propenoic acid tri(cyclohexylammonium) salt, PEP-3CHA, Phosphoenolpyruvic acid tris(cyclohexylamine) salt

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Fórmula empírica (notación de Hill):
C3H5O6P · 3C6H13N
Número CAS:
Peso molecular:
465.56
NACRES:
NA.83
PubChem Substance ID:
UNSPSC Code:
12352204
EC Number:
252-618-7
MDL number:
Beilstein/REAXYS Number:
3752336
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Nombre del producto

Phospho(enol)pyruvic acid tri(cyclohexylammonium) salt, ≥98% (enzymatic)

Quality Level

assay

≥98% (enzymatic)

form

powder

solubility

water: 100 mg/mL, clear to 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

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.


Clase de almacenamiento

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)



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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)
Secretion from dense granules
Methods in Molecular biology: Platelets and Megakaryocytes, volume 1, functional assays, 89-91 (2004)
Determination of Fructokinase Activity from Zobellia galactanivorans
Groisillier A and Tonon T
Bio-protocol, 5(21), e1633-e1633 (2015)