17177-50-3Relevant articles and documents
Mechanisms of formation of adducts from reactions of glycidaldehyde with 2′-deoxyguanosine and/or guanosine
Golding, Bernard T.,Slaich, Pritpal K.,Kennedy, Gordon,Bleasdale, Christine,Watson, William P.
, p. 147 - 157 (1996)
Convenient syntheses of rac-glycidaldehyde from rac-but-3-ene-1,2-diol and (R)-glycidaldehyde from D-mannitol are described. (R)-Glycidaldehyde (1) reacts with guanosine in water (pH 4-11, faster reaction at higher pH) to give initially 6(S)-hydroxy-7(S)-(hydroxymethyl)-3-(β-D-ribofuranosyl)-5,6,7- trihydroimidazo[1,2-a]purin-9(3H)-one (7a) and 6(S),7(R)-dihydroxy-3-(β-D-ribofuranosyl)-5,6,73-tetrahydropyrimido[1,2-a] purin-10(3H)-one (8a). The former decomposes to 7-(hydroxymethyl)-5,9-dihydro-9-oxo-3-(β-D-ribofuranosyl)imidazo[1,2-a] purine (3a), 5,9-dihydro-9-oxo-3-(β-D-ribofuranosyl)imidazo[1,2-a]purine (5a, 1,N2-ethenoguanosine), and formaldehyde, while the latter adduct is relatively stable. The position of the hydroxymethyl group on the imidazo ring of 7-(hydroxymethyl)-5,9-dihydro-9-oxo-3-(β-D-ribofuranosyl)imidazo-[1,2-a] purine was proved by 13C NMR analysis of adducts derived from [1-15N]guanosine and [amino-15N]guanosine. At longer reaction times, the adduct 7,7′-methylenebis[5,9-dihydro-9-oxo-3-(β-D-ribofuranosyl)imidazo[1,2- a]purine[ (4a) is formed from guanosine and glycidaldehyde. The structure analysis of this adduct was also aided by 13C NMR analysis of the 15N-labeled adduct derived from [1-15N]guanosine. Analogous adducts were obtained from the reaction between glycidaldehyde and deoxyguanosine. Mechanisms of formation of the adducts from glycidaldehyde and guanosine/deoxyguanosine are proposed and supported by model studies with simple amines. The formaldehyde produced in the reactions described reacts with guanosine to give the known adduct N2-(hydroxymethyl)guanosine (9).
In vitro and in vivo mutagenicity of the butadiene metabolites butadiene diolepoxide, butadiene monoepoxide and diepoxybutane
Adler,Kliesch,Nylund,Peltonen
, p. 339 - 345 (1997)
Three metabolites of 1,3-butadiene, namely butadiene diolepoxide, butadiene monoepoxide and diepoxybutane, were tested in the bacterial mutation assay using Salmonella typhimurium Strain TA100 with and without metabolic activation (S9 mix). All three compounds showed a mutagenic response. The bifunctional epoxide was more effective than the diolepoxide which was more effective than the monoepoxide. Toxicity appeared to follow the ranking of the chemicals for their mutagenic potency. The monoepoxide and the diolepoxide were also tested for induction of micronuclei in mouse bone marrow erythrocytes and for dominant lethal mutation induction in postmeiotic male mouse germ cells. The effects of the diepoxide in both in vivo tests have been published earlier. In the micronucleus assay, the three metabolites gave a positive response whereby the diepoxide was more effective than the monoepoxide which was more effective than the diolepoxide. In contrast to the diepoxide which was positive at a dose as low as 36 mg/kg, the monoepoxide and the diol did not show an induction of dominant lethal effects up to doses of 120 and 240 mg/kg, respectively. It is concluded that the metabolites were mutagenic in bacteria without metabolic activation and clastogenic in mouse bone marrow; only the bifunctional diepoxide, however, was active in postmeiotic male mouse germ cells.
Preparation of 2,3,4-trihydroxybutylarsonic acid: A starting compound for novel arsonolipids
Lala, Maria A.,Tsivgoulis, Gerasimos M.,Ioannou, Panayiotis V.
, p. 2747 - 2760 (2008/12/22)
Possible routes for the preparation of 2,3,4-trihydroxybutylarsonic acid, a key compound for the synthesis of novel arsonolipids, were experimentally evaluated. The best substrate was found to be 3,4-epoxybutane-1,2-diol. Its reaction with alkaline sodium arsenite, "Na3AsO3," gave the arsonic acid in 50% yield, as two pairs of diastereoisomers, each pair being a racemic mixture. Copyright Taylor & Francis Group, LLC.
