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43517

Sigma-Aldrich

Glycolaldehyde 2-phosphate calcium salt

≥95.0% (TLC)

Synonym(s):

2-(Phosphonooxy)acetaldehyde calcium salt, Phosphoric acid mono(2-oxoethyl) ester calcium salt

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About This Item

Empirical Formula (Hill Notation):
C2H3CaO5P
Molecular Weight:
178.09
Beilstein/REAXYS Number:
4277948
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.24

assay

≥95.0% (TLC)

concentration

16-22% Ca

format

neat

storage temp.

−20°C

SMILES string

O=C([H])COP([O-])([O-])=O.[Ca+2]

InChI

1S/C2H5O5P.Ca/c3-1-2-7-8(4,5)6;/h1H,2H2,(H2,4,5,6);/q;+2/p-2

InChI key

GDJKIYUDRLVKJE-UHFFFAOYSA-L

Biochem/physiol Actions

Oxidation of both the 2′- and 3′-positions of 2-deoxyribose can lead to the formation of the reactive electrophilic 2-phosphoglycolaldehyde which readily forms adducts with neighboring DNA bases, aldolase substrate

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable


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Georges A Lahoud et al.
Chemical research in toxicology, 19(12), 1630-1636 (2006-12-19)
Oxidative events that target the sugar-phosphate backbone of DNA can lead to reactive fragments that interfere with DNA repair, transcription and translation by the formation of cross-links and adducts of proteins and nucleobases. Here we report the formation of several
Regulation of aspartate aminotransferase isozymes by D-erythrose 4-phosphate and glycolaldehyde phosphate, the naturally occurring homologues of D-glyceraldehyde 3-phosphate.
L Kopelovich et al.
The Journal of biological chemistry, 247(10), 3262-3268 (1972-05-25)
R Krishnamurthy et al.
Origins of life and evolution of the biosphere : the journal of the International Society for the Study of the Origin of Life, 29(4), 333-354 (1999-09-03)
Amidotriphosphate (0.1 M) in aqueous solution at near neutral pH in the presence of magnesium ions (0.25 M) converts glycolaldehyde (0.025 M) within days at room temperature into glycolaldehyde phosphate in (analytically) nearly quantitative yields (76% in isolated product). This
Glycolaldehyde and glycolaldehyde phosphate as reaction components in enzymatic pentose formation.
J MARMUR et al.
Archives of biochemistry and biophysics, 31(1), 154-155 (1951-03-01)
M Awada et al.
Chemical research in toxicology, 14(9), 1247-1253 (2001-09-18)
Oxidation of deoxyribose in DNA results in the formation of a variety of electrophilic products that have the potential to react with nucleobases to form adducts. We now report that 2-phosphoglycolaldehyde, a model for the 3'-phosphoglycolaldehyde residue generated by 3'-oxidation

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