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1 Acta Biochimica Polonica

1 1996

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Synthesis and application of novel nucleoside phosphonates and phosphoramidites modified at the base moiety

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Seela F. , Chen Y. , Melenewski A. , Rosemeyer H. , Wei C.

nr 1

The H-phosphonates and phosphoramidites of 2'-deoxyisoguanosine, 2'-deoxy- isoinosine, 5-aza-7-deaza-2'-deoxyguanosine, and \:1-methyl-2'-deoxyformycin A were prepared. The diphenylcarbamoyl group was chosen for the 2-O-protection of 2'-deoxyisoinosine and 2'-deoxyisoguanosine, and dimethylaminoalkylidene groups were used to block the amino function of the various monomers. The synthesis of isoguanine oligonucleotides was found to be much more efficient using the 2-O-protected building blocks compared to those without oxygen protection. Oligodeoxynucleotides containing 2-deoxyisoguanosine and 2'-deoxycytidine form parallel duplex structures. The self-complementary duplex containing 5-aza-7-deaza- 2'-deoxyguanosine and 2'-deoxycytidine forms a stable duplex in acidic solution (pH = 5.0) while it is destabilized under neutral conditions.