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P7252

Sigma-Aldrich

Phospho(enol)pyruvic acid tri(cyclohexylammonium) salt

≥98% (enzymatic), powder

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C3H5O6P · 3C6H13N
CAS Number:
35556-70-8
Molecular Weight:
465.56
Beilstein/REAXYS Number:
3752336
EC Number:
252-618-7
MDL number:
MFCD00004258
UNSPSC Code:
12352204
PubChem Substance ID:
24898831
NACRES:
NA.83

product name

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

Quality Level

200

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.

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Determination of Fructokinase Activity from Zobellia galactanivorans
Groisillier A and Tonon T
Bio-protocol, 5(21), e1633-e1633 (2015)
Structural basis for kinase-mediated macrolide antibiotic resistance
Fong DH, et al.
Structure, 25(5), 750-761 (2017)
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)
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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