ISSN:
0018-019X
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
The 1,7-dideaza-2′-deoxyadenosine (c1c7Ad; 1) was converted into building blocks 3a,b for solid-phase oligodeoxyribonucleotide synthesis. Testing various N-protecting groups - benzoyl, phenoxyacetyl, [(fluoren-9-yl)methoxy]carbonyl, and (dimethylamino)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 c1c7Ad and dT residues (7 and 8) as well as palindromic oligomers such as d(C-G-C-G-c1c7 A-c1c7 A-T-T-C-G-C-G) (10) and d(G-T-A-G-c1c7 A-c1c7 A-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.
Additional Material:
5 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hlca.19920750414
