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P3637

Sigma-Aldrich

Phospho(enol)pyruvic acid cyclohexylammonium salt

≥97% (enzymatic)

Synonym(s):

2-(Phosphonooxy)-2-propenoic acid monopotassium salt

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About This Item

Empirical Formula (Hill Notation):
C3H4O6P · C6H14N
CAS Number:
Molecular Weight:
267.22
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Assay

≥97% (enzymatic)

form

powder

storage temp.

−20°C

SMILES string

NC1CCCCC1.OC(=O)C(=C)OP(O)(O)=O

InChI

1S/C6H13N.C3H5O6P/c7-6-4-2-1-3-5-6;1-2(3(4)5)9-10(6,7)8/h6H,1-5,7H2;1H2,(H,4,5)(H2,6,7,8)

InChI key

VHFCNZDHPABZJO-UHFFFAOYSA-N

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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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).
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
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)

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