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1,7-Dideaza-2′-deoxyadenosine: Building blocks for solid-phase synthesis and secondary structure of base-modified oligodeoxyribonucleotides

✍ Scribed by Frank Seela; Thomas Wenzel

Publisher
John Wiley and Sons
Year
1992
Tongue
German
Weight
743 KB
Volume
75
Category
Article
ISSN
0018-019X

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✦ Synopsis

Dedicated to Prof. W. Pfeiderer on the occasion of his 65th birthday (3. IV. 92)

The 1,7-dideaza-2'-deoxyadenosine (c'c7A,; 1) was converted into building blocks 3a,b for solid-phase oligodeoxyribonucleotide synthesis. Testing various N-protecting groupsbenzoyl, phenoxyacetyl, [(fluoren-9yl)methoxy]carbonyl, and (dimethy1amino)methylidene -only the latter two were found to be suitable (1 + 4b, d). Ensuing 4,4'-dimethoxytritylation of 4d and phosphitylation afforded the 3'-phosphonate 3a or the 3'-[(2-cyanoethyl)diisopropylphosphoramidite] 3b. Self-complementary oligonucleotides with alternating dA or c'c7A, and dT residues (7 and 8) as well as palindromic oligomers such as d(C-G-C-G-c1c7A-c'c7A-T-T-C-G-C-G) (10) and d(G-T-A-G-c1c7A-c'c7A-T-T-C-T-A-C) (12) were synthesized. Duplex stability was decreased because 1 cannot form Watson-Crick or Hoogsteen base pairs if incorporated into oligonucleotides. On the other hand, the structural modifications in 10 and 12 forced these palindromic oligomers to form hairpin structures.

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