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3-Deazaguanine N7- and N9-(2′-Deoxy-β-D-ribofuranosides): Building Blocks for Solid-Phase Synthesis and Incorporation into Oligodeoxyribonucleotides

✍ Scribed by Frank Seela; Sigrid Lampe

Publisher
John Wiley and Sons
Year
1991
Tongue
German
Weight
663 KB
Volume
74
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

Oligonucleotides continuing 3‐deaza‐2′‐deoxyguanosine (I) or its N^7^‐regioisomer 2 were prepared by solid‐phase synthesis using P^111^ chemistry. Protection of ^1^ or ^2^ with N,N V‐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 10__c__ or lie, respectively; the cyanoethyl N,N‐diisopropylphosphoramidite 10d was also prepared. The oligonucleotide building blocks were employed in automated solid‐phase synthesis. 1 he 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.

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