8-AZA-2'-DEOXYGUANOSINE AND RELATED 1,2,3-TRIAZOLO[4,5-D]PYRIMIDINE 2'-DEOXYRIBOFURANOSIDES

Autor(en): SEELA, F
LAMPE, S
Stichwörter: 8-AZAPURINES; Chemistry; Chemistry, Multidisciplinary
Erscheinungsdatum: 1993
Herausgeber: NEW SWISS CHEMICAL SOC
Journal: HELVETICA CHIMICA ACTA
Volumen: 76
Ausgabe: 6
Startseite: 2388
Seitenende: 2397
Zusammenfassung: 
The synthesis of 8-azaguanine N-9-, N8-, and N7-(2'-deoxyribonucleosides) 1-3, related to 2'-deoxyguanosine (4), is described. Glycosylation of the anion of 5-amino-7-methoxy-3H-1,2,3-triazolo[4,5-d]pyrimidine (5) with 2-deoxy-3,5-di-O-(4-toluoyl)-alpha-D-erythro-pentofuranosyl chloride (6) afforded the regioisomeric glycosylation products 7a/7b, 8a/8b, and 9 (Scheme 1) which were detoluoylated to give 10a, 10b, 11a, 11b, and 12a. The anomeric configuration as well as the position of glycosylation were determined by combination of UV, C-13-NMR, and H-1-NMR NOE-difference spectroscopy. The 2-amino-8-aza-2'-deoxyadenosine (13), obtained from 7a, was deaminated by adenosine deaminase to yield 8-aza-2'-deoxyguanosine (1), whereas the N7- and N8-regioisomers were no substrates of the enzyme. The N-glycosylic bond of compound 1 (0.1 N HCl) is ca. 10 times more stable than that of 2'-deoxyguanosine (4).
ISSN: 0018019X
DOI: 10.1002/hlca.19930760625

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