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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:
4277948
UNSPSC Code:
12352200
PubChem Substance ID:
329756345
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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
BCBP8821V
BCBP8821

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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
Chemistry of α-Aminonitriles. Part 13. Formation of 2-Oxoethyl phosphates ('glycolaldehyde phosphates') from rac-Oxiranecarbonitrile and inorganic phosphate and on (formal) constitutional relationships between 2-Oxoethyl phosphates and oligo (hexo- and pentopyranosyl)nucleotide backbones.
Pitsch, S., et al.
Helvetica Chimica Acta, 77, 2251-2285 (1994)
Chemistry of α-Aminonitriles. Aldomerisation of Glycolaldehyde Phosphate to rac-Hexose 2,4,6-Triphosphates and (in Presence of Formaldehyde) rac-Pentose 2,4-Diphosphates: rac-Allose 2,4,6-Triphosphate and rac-Ribose 2,4-Diphosphate Are the Main Reaction Products.
Mueller, D., et al.
Helvetica Chimica Acta, 73, 1410-1468 (1990)
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
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)
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