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P0564

Sigma-Aldrich

Phospho(enol)pyruvic acid monosodium salt hydrate

≥97% (enzymatic)

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Synonym(s):
2-(Phosphonooxy)-2-propenoic acid monosodium, mono-Sodium phosphoenolpyruvate hydrate, Monosodium phosphoenolpyruvate
Empirical Formula (Hill Notation):
C3H4NaO6P · xH2O
CAS Number:
Molecular Weight:
190.02 (anhydrous basis)
Beilstein:
4771585
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

Assay

≥97% (enzymatic)

form

powder

storage temp.

−20°C

SMILES string

O.[Na+].OC(=O)C(=C)OP(O)([O-])=O

InChI

1S/C3H5O6P.Na.H2O/c1-2(3(4)5)9-10(6,7)8;;/h1H2,(H,4,5)(H2,6,7,8);;1H2/q;+1;/p-1

InChI key

YEQQMAFLJISSCR-UHFFFAOYSA-M

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Biochem/physiol Actions

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.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Kristina Vogel et al.
International journal of molecular sciences, 21(21) (2020-10-30)
For systems biology, it is important to describe the kinetic and thermodynamic properties of enzyme-catalyzed reactions and reaction cascades quantitatively under conditions prevailing in the cytoplasm. While in part I kinetic models based on irreversible thermodynamics were tested, here in
Rewiring of glycolysis in cancer cell metabolism.
Jason W Locasale et al.
Cell cycle (Georgetown, Tex.), 9(21), 4253-4253 (2010-11-04)
Biosynthesis of aromatic amino acids by highly purified spinach chloroplasts. Compartmentation and regulation of the reactions.
Bagge, P. and Larsson, C.
Physiologia Plantarum, 68, 641-647 (1986)
Uwe Sauer et al.
FEMS microbiology reviews, 29(4), 765-794 (2005-08-17)
In many organisms, metabolite interconversion at the phosphoenolpyruvate (PEP)-pyruvate-oxaloacetate node involves a structurally entangled set of reactions that interconnects the major pathways of carbon metabolism and thus, is responsible for the distribution of the carbon flux among catabolism, anabolism and
Marcel Emmerling et al.
Journal of bacteriology, 184(1), 152-164 (2001-12-14)
The intracellular carbon flux distribution in wild-type and pyruvate kinase-deficient Escherichia coli was estimated using biosynthetically directed fractional 13C labeling experiments with [U-13C6]glucose in glucose- or ammonia-limited chemostats, two-dimensional nuclear magnetic resonance (NMR) spectroscopy of cellular amino acids, and a

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