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D7137

Sigma-Aldrich

Dihydroxyacetone phosphate dilithium salt

≥93% dry basis (enzymatic)

Synonym(s):

1,3-Dihydroxy-2-propanone 1-phosphate dilithium salt, 1-Hydroxy-3-(phosphonooxy)-2-propanone dilithium salt, DHAP

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About This Item

Empirical Formula (Hill Notation):
C3H5Li2O6P
CAS Number:
102783-56-2
Molecular Weight:
181.92
Beilstein/REAXYS Number:
1708891
MDL number:
MFCD00077731
UNSPSC Code:
12352201
PubChem Substance ID:
24894082
NACRES:
NA.25

biological source

bovine (casein)

Quality Level

200

assay

≥93% dry basis (enzymatic)

form

powder

impurities

~0.2 mol % D-glyceraldehyde 3-phosphate

color

white

solubility

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

anion traces

phosphate (PO43-): ~5 mol %

cation traces

Li: 5.5-8.0% (dry basis)

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.

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

To gain a comprehensive understanding of our extensive range of Monosaccharides for your research, we encourage you to visit our Carbohydrates Category page.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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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M Merced Malabanan et al.
Journal of the American Chemical Society, 133(41), 16428-16431 (2011-09-24)
The L232A mutation in triosephosphate isomerase (TIM) from Trypanosoma brucei brucei results in a small 6-fold decrease in k(cat)/K(m) for the reversible enzyme-catalyzed isomerization of glyceraldehyde 3-phosphate to give dihydroxyacetone phosphate. In contrast, this mutation leads to a 17-fold increase
Virginia De Cesare et al.
Cell chemical biology, 25(9), 1117-1127 (2018-07-19)
Due to their role in many diseases, enzymes of the ubiquitin system have recently become interesting drug targets. Despite efforts, primary screenings of compound libraries targeting E2 enzymes and E3 ligases have been strongly limited by the lack of robust
Valentina Piano et al.
Biochemical and biophysical research communications, 481(1-2), 51-58 (2016-11-12)
Although the precise functions of ether phospholipids are still poorly understood, significant alterations in their physiological levels are associated either to inherited disorders or to aggressive metastatic cancer. The essential precursor, alkyl-dihydroxyacetone phosphate (DHAP), for all ether phospholipids species is
Nasser M Al-Daghri et al.
Scientific reports, 7(1), 12633-12633 (2017-10-05)
Obesity is a pathological condition caused by genetic and environmental factors, including vitamin D deficiency, which increases the risk of developing cardiovascular disorders and diabetes. This case-control study was designed to verify whether serum profiles could be identified differentiating obese
Baek-Rock Oh et al.
Microbial cell factories, 17(1), 92-92 (2018-06-17)
1,3-Propanediol (1,3-PDO) is important building blocks for the bio-based chemical industry, Klebsiella pneumoniae can be an attractive candidate for their production. However, 1,3-PDO production is high but productivity is generally low by K. pneumoniae. In this study, repeated fed-batch cultivation
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