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02711

Sigma-Aldrich

Hydroxypyruvic acid phosphate lithium salt

≥95% (HPLC)

Synonym(s):

2-oxo-3-(phosphonooxy)propanoic acid, Phosphohydroxypyruvic acid

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About This Item

Empirical Formula (Hill Notation):
C3H5O7P · xLi+
CAS Number:
Molecular Weight:
184.04 (free acid basis)
MDL number:
UNSPSC Code:
12352106
PubChem Substance ID:
NACRES:
NA.25

Quality Level

Assay

≥95% (HPLC)

composition

lithium, 5.0-14.0% ICP

impurities

≤8.0% water

storage temp.

−20°C

SMILES string

O=C(O)C(COP(O)(O)=O)=O

InChI

1S/C3H5O7P/c4-2(3(5)6)1-10-11(7,8)9/h1H2,(H,5,6)(H2,7,8,9)

InChI key

LFLUCDOSQPJJBE-UHFFFAOYSA-N

Biochem/physiol Actions

L-Serine may be derived from four possible sources: dietary intake, biosynthesis from the glycolytic intermediate 3-phosphoglycerate, from glycine, and by protein and phospholipid degradation. In the biosynthetic pathway, the glycolytic intermediate 3-phosphoglycerate is converted into phosphohydroxy-pyruvate, in a reaction catalyzed by 3-phosphoglycerate dehydrogenase (3- PGDH; EC 1.1.1.95). Phosphohydroxypyruvate is metabolized to phosphoserine by phosphohydroxypyruvate aminotransferase (EC 2.6.1.52) and, finally, phosphoserine is converted into L-serine by phosphoserine phosphatase (PSP; EC 3.1.3.3). In liver tissue, the serine biosynthetic pathway is regulated in response to dietary and hormonal changes. Of the three synthetic enzymes, the properties of 3-PGDH and PSP are the best documented. Hormonal factors such as glucagon and corticosteroids also influence 3-PGDH and PSP activities in interactions dependent upon the diet. L-serine plays a central role in cellular proliferation. L-Serine is the predominant source of one-carbon groups for the de novo synthesis of purine nucleotides and deoxythymidine monophosphate. It has long been recognized that, in cell cultures, L-serine is a conditional essential amino acid, because it cannot be synthesized in sufficient quantities to meet the cellular demands for its utilization. In recent years, L-serine and the products of its metabolism have been recognized not only to be essential for cell proliferation, but also to be necessary for specific functions in the central nervous system. The findings of altered levels of serine and glycine in patients with psychiatric disorders and the severe neurological abnormalities in patients with defects of L-serine synthesis underscore the importance of L-serine in brain development and function; e.g. Alzheimer′s disease, schizophrenia, heart failure, and juvenile myoclonic epilepsy.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Oral

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


Certificates of Analysis (COA)

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K Q Do et al.
Journal of neurochemistry, 65(6), 2652-2662 (1995-12-01)
HPLC and gas chromatography-mass spectrometry analyses of 18 amino acids, N-acetylaspartate, N-acetylaspartylglutamate, and 5-hydroxyindoleacetic acid, derived from serotonin, and homovanillic acid, derived from dopamine, were performed in CSF collected from a group of patients with schizophrenia who either had been
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Archives of general psychiatry, 60(6), 572-576 (2003-06-11)
The hypofunction of the N-methyl-D-aspartate (NMDA) subtype of glutamate receptors has been implicated in the pathophysiology of schizophrenia. Several lines of evidence suggest that D-serine may function as an endogenous agonist of the glycine site of the NMDA receptor. The
H Nørrelund et al.
Journal of internal medicine, 260(1), 11-21 (2006-06-23)
It is well known that chronic heart failure (CHF) is associated with insulin resistance and cachexia, but little is known about the underlying substrate metabolism. The present study was undertaken to identify disturbances of basal glucose, lipid and protein metabolism.
Sirpa Rainesalo et al.
Neurochemical research, 29(1), 319-324 (2004-03-03)
Altered plasma and cerebrospinal fluid amino acid levels may be associated with human epilepsy. We studied three groups of patients, those with a generalized epileptic syndrome, juvenile myoclonic epilepsy, patients with refractory localization-related epilepsies, and patients with acute seizures (within
A N Fonteh et al.
Amino acids, 32(2), 213-224 (2006-10-13)
Our aim was to determine changes in free amino acid (FAA) and dipeptide (DP) concentrations in probable Alzheimer's disease (pAD) subjects compared with control (CT) subjects using liquid chromatography and electrospray ionization tandem mass spectrometry (LCMS2). We recruited gender- and

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