2'-DEOXYISOGUANOSINE AND BASE-MODIFIED ANALOGS - CHEMICAL AND PHOTOCHEMICAL-SYNTHESIS

Autor(en): KAZIMIERCZUK, Z
MERTENS, R
KAWCZYNSKI, W
SEELA, F
Stichwörter: 2'-DEOXYRIBOFURANOSIDES; Chemistry; Chemistry, Multidisciplinary; DNA; ENZYMATIC INCORPORATION; GLYCOSYLATION; ISOGUANOSINE; NUCLEOBASE; PAIR; RNA
Erscheinungsdatum: 1991
Herausgeber: NEW SWISS CHEMICAL SOC
Journal: HELVETICA CHIMICA ACTA
Volumen: 74
Ausgabe: 8
Startseite: 1742
Seitenende: 1748
Zusammenfassung: 
The synthesis of 2'-deoxyisoguanosine (2), and the pyrrolo[2,3-d]pyrimidine and pyrazolo[3,4-d]pyrimidine 2'-deoxyribonucleosides 3 and 4 is described. Condensation of the imidazole precursor 5 with benzoyl isocyanate followed by reaction with ammonia gave 2. Its N(7) regioisomer was obtained from 6. Compound 2 was also prepared by the photochemically induced conversion of 2-chloro- and 2-bromopurine 2'-deoxyribofuranosides 9a and 10, respectively, in aqueous solution. The photo reaction was further used for the synthesis of the compounds 3 and 4 starting with the amino-chloro-2'-deoxynucleosides 9b and 9c, respectively.
ISSN: 0018019X
DOI: 10.1002/hlca.19910740816

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