Synthesis and Properties of Deoxyoligonucleotides Containing Putrescinylthymine : Nucleosides and Nucleotides. LXXVI(Organic,Chemical)

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Putrescinylthymidine was prepared by the reduction of the Schiff base formed from a 2'-deoxy-5-formyluridine derivative and N-phthaloylputrescine, followed by deprotection. The following deoxyoligonucleotides containing putrescinylthymine (T^p) were synthesized; dodecathymidylic acids containing two to four T^p residues, self-complementary decanucleotides (AAGAATTCTT) and dodecanucleotides (AGATAGCTATCT) in which T residues were partly replaced by T^p, and related oligomers. Oligonucleotides containing T^p were resistant to nuclease Sl digestion and were poor substrates to venom phosphodiesterase. The thermal stability (T_m) of the duplex structure of oligomers containing T^p was not enhanced in spite of the expected electrostatic binding between the putrescinyl and phosphoryl residues, and was rather sequence-dependent.
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1987-09-25