α-Oligodeoxynucleotides Containing 5-Propynyl Analogs of α-Deoxyuridine and α-Deoxycytidine: Synthesis and Base Pairing Properties

Article abstract of DOI:10.1016/S0040-4020(97)10258-7

From propyne and 5-iodo-α,2-deoxyuidine, obtained by glycosylation, 5-propynyl-α,2'-deoxyuridine was synthesized following the procedure of Hobbs.One part was then transformed through displacement of its C4-triazolo derivative with ammonia into 5-propynyl-α,2'-deoxycytidine derivative.Finally, the corresponding α 5-propynyl nucleoside phosphoramidites were prepared, and 5-propynyl-α oligonucleotides (12-mer) with either phosphodiester and phosphorothioate were synthesized.The melting temperatures showed that duplexes with complementary DNA are stabilized between 0.65 and 1.2 deg C/mod, and duplexes with RNA are stabilized between 1.2 and 1.4 deg C/mod.