ISSN:
0018-019X
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
The synthesis of oligonucleotides containing 7-(2-deoxy-β -D-erythro-pentofuranosyl)adenine (N7Ad; 1) is described. Compound 1 was obtained from the precursor 4-amino-1H -imidazole-5-carbonitrile 2-deoxyribonucleoside 6 and was found to be much more labile than Ad. The N6-benzoyl protecting group (see 8) destabilized the N-glycosylic bond further and was difficult to remove by NH3-catalyzed hydrolysis. Therefore, a (dimethyl-amino)methylidene residue was introduced (→9). Amidine 9 was blocked at OH—C(5′) with the dimethoxytrityl residue ((MeO)2Tr), and phosphonate 4 as well as phosphoramidite 5 were prepared under standard conditions. Phosphonate 4 was employed in solid-phase oligonucleotide synthesis. Homooligonucleotides as well as self-complementary oligonucleotides were prepared. The oligomer d[(N7A)11-A] (11) formed a duplex with d(T12) (13). Antiparallel chain polarity and reverse Watson-Crick base pairing was deduced from duplex formation of the self-complementary d[(N7A)8-T8] (14).
Additional Material:
8 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hlca.19940770302
