Synthesis of boranoate, selenoate, and thioate analogs of AZTp4A and Ap4A

We report efficient, one-flask procedures for the synthesis of a family of 14 analogs of AZTp4A and Ap4A containing BH3, S, or Se, along with two bisphosphonate analogs of Ap4A. These compounds should slow unwanted enzymatic hydrolysis and have the potential to create unique binding interactions in biochemical and structural studies of the excision reaction responsible for resistance of HIV-1 to AZT, as well as assist in drug design.