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Titolo:
SYNTHESIS OF MULTIPLY-LABELED [N-15(3),C-13(1)]-8-OXO SUBSTITUTED PURINE-BASES AND THEIR CORRESPONDING 2'-DEOXYNUCLEOSIDES
Autore:
STADLER RH; STAEMPFLI AA; FAY LB; TURESKY RJ; WELTI DH;
Indirizzi:
NESTEC LTD,NESTLE RES CTR,VERS CHEZ LES BLANC,POB 44 CH-1000 LAUSANNE26 SWITZERLAND
Titolo Testata:
Chemical research in toxicology
fascicolo: 6, volume: 7, anno: 1994,
pagine: 784 - 791
SICI:
0893-228X(1994)7:6<784:SOM[SP>2.0.ZU;2-5
Fonte:
ISI
Lingua:
ENG
Soggetto:
OXIDATIVE DAMAGE; HYDROGEN-PEROXIDE; NITROGEN-15-LABELED DEOXYNUCLEOSIDES; DNA TEMPLATES; 8-HYDROXY-2'-DEOXYGUANOSINE; MUTAGENESIS; ACID; 8-HYDROXYDEOXYGUANOSINE; DEOXYGUANOSINE; DEOXYADENOSINE;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Science Citation Index Expanded
Science Citation Index Expanded
Citazioni:
45
Recensione:
Indirizzi per estratti:
Citazione:
R.H. Stadler et al., "SYNTHESIS OF MULTIPLY-LABELED [N-15(3),C-13(1)]-8-OXO SUBSTITUTED PURINE-BASES AND THEIR CORRESPONDING 2'-DEOXYNUCLEOSIDES", Chemical research in toxicology, 7(6), 1994, pp. 784-791

Abstract

Stable isotope-labeled analogues of oxidatively modified purine basesare required as internal standards for accurate quantitation of free radical induced damage in DNA using the isotope-dilution GC/MS technique. For this reason, we report on a facile and expedient method to synthesize the isotope-labeled oxidized DNA bases 8-oxoguanine (8-oxo-Gua, 5a) and 8-oxoadenine (8-oxo-Ade, 5b). Both routes have in common theintroduction of two exocyclic N-15 isotopes simultaneously by halogendisplacement of chlorine-substituted pyrimidines,vith [N-15]- benzylamine. Debenzylation is achieved by either catalytic hydrogenation or treatment with aluminium chloride in benzene. An additional isotope is incorporated by nitrosation with N-15- labeled sodium nitrite. Cyclocondensation of the triamines with C-13-labeled urea then affords 5a and5b in overall yields of 34% and 27%, respectively, and each with fourisotope labels and at least 99 atom % excess. A further one-step enzyme catalyzed coupling of the C8 adducted purines with 2'-deoxyribose furnishes the isotope-labeled 2'-deoxynucleosides 2'-deoxy-7,8-dihydro-8-oxoguanosine (8-oxo-dGuo) and 2'-deoxy-7,8-dihydro-8-oxoadenosine (8-oxo-dAdo).

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 11/07/20 alle ore 02:52:11