Peptide-Nucleoside Conjugates: Synthesis and Anti-HIV Activities

Abstract New peptide-nucleosides which consist of an anti-RT nucleoside and anti-protease peptide moieties, were designed in order to investigate their anti-HIV-1 properties. The synthesis of these new analogues was achieved using BOP coupling reagent which avoided the protection and deprotection steps of the 5′-OH group of the nucleoside part. These new compounds tested on MT4 infected cells show no increase in anti-HIV activities compared to that of the component pieces. Interestingly we found that the 5′-(tert-butyldiphenyl)silyl analogues show anti-HIV activities equivalent to that of the 5′-free OH corresponding compounds. This result suggests a possible interaction of these compounds at a non-substrate binding site of the reverse transcriptase.