SYNTHESIS AND HYBRIDIZATION PROPERTIES OF BETA-OLIGODEOXYNUCLEOTIDES AND ALPHA-OLIGODEOXYNUCLEOTIDES CONTAINING 3-C-ALLYL-2-DEOXY-D-ERYTHRO-PENTOFURANOSYL)THYMINE AND 3-C-ALLYL-2-DEOXY-D-ERYTHRO-PENTOFURANOSYL)THYMINE AND NOPROPYL)-2-DEOXY-D-ERYTHRO-PENTOFURANOSYL]THYMINE

Convergent synthesis of beta- and 3-C-allyl-2-deoxy-D-erythro-pentofur anosyl)thymine and their incorporation into beta- and alpha-oligodeoxy nucleotides (ODNs) is described.:The thermal stabilities of duplexes f ormed between modified ODNs and complementary single-stranded DNA and RNA have been evaluated. In all cases stable duplexes are formed, but whereas beta-ODNs containing beta-3'-C-allylthymidine show moderately lowered thermal stability towards both DNA and RNA, alpha-ODNs contain ing a-3'-C-allylthymidine show significantly increased thermal stabili ties compared with the corresponding beta-ODN reference duplexes. Even more stable duplexes towards both DNA and RNA have been obtained usin g an alpha-ODN containing one nopropyl)-2-deoxy-D-erythro-pentofuranos yl]thymine monomer.