F. Seela, W. Herdering, A. Kehne
Sep 23, 1987
Citations
0
Influential Citations
21
Citations
Journal
Helvetica Chimica Acta
Abstract
N6-(Carbamoylmethyl)-2′-deoxyadenosine (1), a modified nucleoside occurring in bacteriophage Mu, was synthesized by two different routes. Glycinamide was introdued by nucleophilic displacement of(2,4,6,-triisopro-pylphenyl)sulfonyloxy or ethylsulfinyl groups at C(6) of the purine moiety. Compound 1 was converted into the protected phosphoramidite 6b and employed in solid-phase synthesis of the self-complementary oligonucleotides 7–14. Replacement of 2′-deoxyadenosine by 1 led to a strong decrease of the Tm values of the oligomers d(A-T)6 (7) and d(A-T-G-A-A-G-C-T-T-C-A-T)(10), respectively. As the oligemer 10 contains the recognition site d(A-A-G-C-T-T) of the endodeoxyribonuclease Hind III, it was subjected to sequence-specific hydrolysis experiments. Replacement of the first or second Ad by 1 prevented enzymatic phosphodiester hydrolysis (results with 11 and 12). In contrast, slow hydrolysis was observed if the less bulky N6-methyl-2′-deoxyadenosine replaced the second Ad residue (results with 14).