43517
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
NACRES:
NA.24
PubChem Substance ID:
UNSPSC Code:
12352200
Beilstein/REAXYS Number:
4277948
InChI
1S/C2H5O5P.Ca/c3-1-2-7-8(4,5)6;/h1H,2H2,(H2,4,5,6);/q;+2/p-2
SMILES string
O=C([H])COP([O-])([O-])=O.[Ca+2]
InChI key
GDJKIYUDRLVKJE-UHFFFAOYSA-L
assay
≥95.0% (TLC)
concentration
16-22% Ca
format
neat
storage temp.
−20°C
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
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
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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)
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)
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
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