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P0564

Sigma-Aldrich

Phospho(enol)pyruvic acid monosodium salt hydrate

≥97% (enzymatic)

Synonym(s):

2-(Phosphonooxy)-2-propenoic acid monosodium, mono-Sodium phosphoenolpyruvate hydrate, Monosodium phosphoenolpyruvate

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About This Item

Empirical Formula (Hill Notation):
C3H4NaO6P · xH2O
CAS Number:
53823-68-0
Molecular Weight:
190.02 (anhydrous basis)
Beilstein:
4771585
EC Number:
258-810-7
MDL number:
MFCD00150738
UNSPSC Code:
12352100
PubChem Substance ID:
57654496
NACRES:
NA.22

Quality Level

200

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.

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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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)
D Allan Butterfield et al.
Journal of neurochemistry, 111(4), 915-933 (2009-09-29)
Enolase enzymes are abundantly expressed, cytosolic carbon-oxygen lyases known for their role in glucose metabolism. Recently, enolase has been shown to possess a variety of different regulatory functions, beyond glycolysis and gluconeogenesis, associated with hypoxia, ischemia, and Alzheimer's disease (AD).
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)
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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