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Titolo:
A NEW ROUTE TO N-15-LABELED, N-ALKYL, AND N-AMINO NUCLEOSIDES VIA N-NITRATION OF URIDINES AND INOSINES
Autore:
ARIZA X; BOU V; VILARRASA J;
Indirizzi:
UNIV BARCELONA,FAC CHEM,DEPT ORGAN CHEM E-08028 BARCELONA SPAIN UNIV BARCELONA,FAC CHEM,DEPT ORGAN CHEM E-08028 BARCELONA SPAIN
Titolo Testata:
Journal of the American Chemical Society
fascicolo: 13, volume: 117, anno: 1995,
pagine: 3665 - 3673
SICI:
0002-7863(1995)117:13<3665:ANRTNN>2.0.ZU;2-#
Fonte:
ISI
Lingua:
ENG
Soggetto:
NITROGEN-15-LABELED OLIGODEOXYNUCLEOTIDES; N-15 NMR; DEOXYNUCLEOSIDES; DERIVATIVES; OLIGONUCLEOTIDES; DEOXYADENOSINE; RESONANCE; RIBONUCLEOSIDE; CONVERSION; BINDING;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Science Citation Index Expanded
Citazioni:
56
Recensione:
Indirizzi per estratti:
Citazione:
X. Ariza et al., "A NEW ROUTE TO N-15-LABELED, N-ALKYL, AND N-AMINO NUCLEOSIDES VIA N-NITRATION OF URIDINES AND INOSINES", Journal of the American Chemical Society, 117(13), 1995, pp. 3665-3673

Abstract

A novel method for the specific [3-N-15]-labeling of pyrimidine nucleosides and [1-N-15]-labeling of purine nucleosides is reported, according to Scheme 1. The N-nitration reaction is carried out in good yields with nitronium trifluoroacetate in cold dichloromethane. Treatment of the resulting N-nitro nucleosides with (NH3)-N-15, alkylamines, or hydrazine cleaves the pyrimidine ring at room temperature, affording open intermediates which undergo cyclization to N-15-labeled, N-alkylated, or N-amino nucleosides, respectively. Preparation of [1-N-15]adenosine from inosine in a 52% overall yield is illustrative of the scope of the procedure. -5'-O-Acetyl-3-amino-2',3'-O-isopropylideneuridine and [1-N-15, (NH2)-N-15]-2',3',5,-tri-O-acetyl-1-aminoinosine have also been obtained from double labeled hydrazine. By using a N-15-labeled substrate and/or N-15-labeled benzylamine it is shown that the amine attack takes mainly place at C4 of uridine and at C2 of inosine.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 13/07/20 alle ore 19:51:29