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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

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

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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Yuval Hart et al.
BMC systems biology, 5, 171-171 (2011-10-26)
C(4) plants such as corn and sugarcane assimilate atmospheric CO(2) into biomass by means of the C(4) carbon fixation pathway. We asked how PEP formation rate, a key step in the carbon fixation pathway, might work at a precise rate
S Mazurek et al.
Journal of bioenergetics and biomembranes, 29(4), 315-330 (1997-08-01)
A common characteristic of tumor cells is the constant overexpression of glycolytic and glutaminolytic enzymes. In tumor cells the hyperactive hexokinase and the partly inactive pyruvate kinase lead to an expansion of all phosphometabolites from glucose 6-phosphate to phosphoenolpyruvate. In
U Theobald et al.
Biotechnology and bioengineering, 55(2), 305-316 (1997-07-20)
The goal of this work was to obtain rapid sampling technique to measure transient metabolites in vivo. First, a pulse of glucose was added to a culture of the yeast Saccharomyces cerevisiae growing aerobically under glucose limitation. Next, samples were
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).
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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