3-DEAZAGUANINE N-7-(2'-DEOXY-BETA-D-RIBOFURANOSIDES) AND N-9-(2'-DEOXY-BETA-D-RIBOFURANOSIDES) - BUILDING-BLOCKS FOR SOLID-PHASE SYNTHESIS AND INCORPORATION INTO OLIGODEOXYRIBONUCLEOTIDES

Autor(en): SEELA, F
LAMPE, S
Stichwörter: ACID; Chemistry; Chemistry, Multidisciplinary; DEOXYADENOSINE; DERIVATIVES; DNA; ECORV RESTRICTION ENDONUCLEASE; GLYCOSYLATION; PRODUCT
Erscheinungsdatum: 1991
Herausgeber: NEW SWISS CHEMICAL SOC
Journal: HELVETICA CHIMICA ACTA
Volumen: 74
Ausgabe: 8
Startseite: 1790
Seitenende: 1800
Zusammenfassung: 
Oligonucleotides containing 3-deaza-2'-deoxyguanosine (1) or its N7-regioisomer 2 were prepared by solid-phase synthesis using P(III) chemistry. Protection of 1 or 2 with N,N-dimethylformamide diethyl acetal followed by 4,4'-dimethoxytritylation afforded imidazo[4,5-c]pyridines 10b and 11b, respectively. The latter were converted into the 3'-phosphonates 10c or 11c, respectively; the cyanoethyl N,N-diisopropylphosphoramidite 10d was also prepared. The oligonucleotide building blocks were employed in automated solid-phase synthesis. The self-complementary oligomers 13, 15, and 17 were prepared and characterized by enzymatic hydrolysis with snake-venom phosphodiesterase followed by alkaline phosphatase. There CD spectra exhibited the general structure of a B-DNA.
ISSN: 0018019X
DOI: 10.1002/hlca.19910740821

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