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Bioorg Med Chem Lett. 2004 Oct 4;14(19):4815-7.

Inhibition of the strand transfer step of HIV-1 integrase by non-natural dinucleotides.

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Department of Pharmaceutical and Biomedical Sciences, University of Georgia, Athens, GA 30602, USA.


New, non-natural dinucleotide 5'-monophosphates, with a surrogate isonucleoside component of l-related stereochemistry at the 'terminal' position, have been synthesized. Structures of 2a-c were confirmed by multinuclear NMR spectra ((1)H, (13)C, (31)P, COSY), UV hypochromicity and FAB HRMS data. These compounds are totally resistant to cleavage by 3'- and 5'-exonucleases. The dinucleotides showed remarkable selectivity for inhibition of the strand transfer step of HIV-1 integrase. To the best of our knowledge, these compounds represent only the second example of selective strand transfer inhibitors of HIV integrase.

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