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Titolo:
MECHANISMS OF FORMATION OF ADDUCTS FROM REACTIONS OF GLYCIDALDEHYDE WITH 2'-DEOXYGUANOSINE AND OR GUANOSINE/
Autore:
GOLDING BT; SLAICH PK; KENNEDY G; BLEASDALE C; WATSON WP;
Indirizzi:
UNIV NEWCASTLE UPON TYNE,DEPT CHEM,BEDSON BLDG NEWCASTLE TYNE NE1 7RUTYNE & WEAR ENGLAND SHELL RES LTD,SITTINGBOURNE RES CTR SITTINGBOURNE ME9 8AG KENT ENGLAND
Titolo Testata:
Chemical research in toxicology
fascicolo: 1, volume: 9, anno: 1996,
pagine: 147 - 157
SICI:
0893-228X(1996)9:1<147:MOFOAF>2.0.ZU;2-A
Fonte:
ISI
Lingua:
ENG
Soggetto:
BISPHENOL-A DIGLYCIDYLETHER; MOLECULAR DOSIMETRY; DNA ADDUCTS; DEOXYGUANOSINE; (R)-GLYCIDALDEHYDE; 2-BROMOACROLEIN; IDENTIFICATION; HYDROLYSIS; PRODUCTS; MOUSE;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Science Citation Index Expanded
Science Citation Index Expanded
Citazioni:
48
Recensione:
Indirizzi per estratti:
Citazione:
B.T. Golding et al., "MECHANISMS OF FORMATION OF ADDUCTS FROM REACTIONS OF GLYCIDALDEHYDE WITH 2'-DEOXYGUANOSINE AND OR GUANOSINE/", Chemical research in toxicology, 9(1), 1996, pp. 147-157

Abstract

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 oxy-7(S)-(hydroxymethyl)3-(beta-D-ribofuranosyl)-5 ,6,7-trihydroimidazo[1,2-a]purin-9(3H)-one (7a) and 6(S), ,6,7,8-tetrahydropyrimidoll[1,2-a]purin-10(3H)-one (8a). The former decomposes to -oxo-3-(beta-D-ribofuranosyl)imidazol[1,2-a]purine (3a), 9-oxo-3-(beta-D-ribofuranosyl)imidazo[1,2-a]purine (5a, 1,N-2-ethenoguanosine), and formaldehyde, while the latter adduct is relatively stable. The position of the hydroxymethyl group on the imidazo ring of -oxo-3-(beta-D-ribofuranosyl)imidazo-[1,2-a]purine was proved by C-13 NMR analysis of adducts derived from [1-N-15]guanosine and [amino-N-15]guanosine. At longer reaction times, the adduct -3-(beta-D-ribofuranosyl)imidazo[1,2-a]purine[(4a) is formed from guanosine and glycidaldehyde. The structure analysis of this adduct was also aided by C-13 NMR analysis of the N-15-labeled adduct derived from [1-N-15]guanosine. Analogousadducts 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 N-2-(hydroxymethyl)guanosine (9).

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Documento generato il 27/09/20 alle ore 00:37:35