D7137

Sigma-Aldrich

Dihydroxyacetone phosphate dilithium salt

≥93% (enzymatic)

Synonym(s):
1,3-Dihydroxy-2-propanone 1-phosphate dilithium salt, DHAP, 1-Hydroxy-3-(phosphonooxy)-2-propanone dilithium salt
Empirical Formula (Hill Notation):
C3H5Li2O6P
CAS Number:
Molecular Weight:
181.92
Beilstein/REAXYS Number:
1708891
MDL number:
PubChem Substance ID:
NACRES:
NA.25

Quality Level

biological source

bovine (casein)

assay

≥93% (enzymatic)

form

powder

impurities

~0.2 mol % D-glyceraldehyde 3-phosphate

solubility

soluble 50mg plus 1ml of H2O, clear, colorless to faintly yellow

anion traces

phosphate (PO43-): ~5 mol %

storage temp.

−20°C

SMILES string

[Li+].[Li+].OCC(=O)COP([O-])([O-])=O

InChI

1S/C3H7O6P.2Li/c4-1-3(5)2-9-10(6,7)8;;/h4H,1-2H2,(H2,6,7,8);;/q;2*+1/p-2

InChI key

QWIKESRFRWLYIA-UHFFFAOYSA-L

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Application

Dihydroxyacetone phosphate (DHAP) is used in fructose metabolism, triose and glycation research. It is used in studies involving the metabolism of three-carbon sugar pools and their roles in physiological and physical processes. DHAP may be used as a substrate to help identify, differentiate and characterize fructose-bisphosphate aldolase(s) (ALDOA) and triosephosphate isomerase(s). DHAP may be used to study cellular glycation stress.

Packaging

5, 10, 25 mg in glass bottle
100, 250 mg in poly bottle

Biochem/physiol Actions

Dihydroxyacetone phosphate (DHAP) is a metabolic intermediate involved in many pathways, including glycolysis, gluconeogenesis, glycerol metabolism, phosphatidic acid synthesis, fat metabolism, and the Calvin cycle.

Caution

Unlike the dimethyl ketal, does not require hydrolysis prior to use as a substrate.

Preparation Note

Enzymatically prepared.

Other Notes

Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. D7137.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis

Certificate of Origin

Chiara Fania et al.
PloS one, 12(6), e0179280-e0179280 (2017-06-20)
In the diagnosis of Alzheimer's disease (AD) total tau (T-tau), tau phosphorylated at threonine 181 (P-tau181), and the 42 amino acid isoform of alpha β-amyloid (Aβ) are well established surrogate CSF markers. However, there is a constant need for new...
Xi Luo et al.
Scientific reports, 7(1), 15170-15170 (2017-11-11)
Matrix-assisted laser desorption/ionization (MALDI) mass spectrometry has been widely used for biomolecular analysis. However, with conventional MALDI, it is difficult to analyse low-molecular-weight compounds because of the interference of matrix ion signals. Here, we report a matrix-free on-chip pulse-heating desorption/ionization...
Daisuke Takagi et al.
Plant & cell physiology, 55(2), 333-340 (2014-01-11)
Sugar-derived reactive carbonyls (RCs), including methylglyoxal (MG), are aggressive by-products of oxidative stress known to impair the functions of multiple proteins. These advanced glycation end-products accumulate in patients with diabetes mellitus and cause major complications, including arteriosclerosis and cardiac insufficiency....
Saheem Ahmad et al.
PloS one, 8(9), e72128-e72128 (2013-09-12)
Non-enzymatic glycation is the addition of free carbonyl group of reducing sugar to the free amino groups of proteins, resulting in the formation of a Schiff base and an Amadori product. Dihydroxyacetone (DHA) is one of the carbonyl species which...
Sebastien Elis et al.
Journal of ovarian research, 10(1), 74-74 (2017-11-11)
Supplementation of bovine oocyte-cumulus complexes during in vitro maturation (IVM) with 1 μM of docosahexaenoic acid (DHA), C22:6 n-3 polyunsaturated fatty acid, was reported to improve in vitro embryo development. The objective of this paper was to decipher the mechanisms of...
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