The Human T cell leukemia virus (HTLV-1) was first isolated from patients with adult T cell leukemia/lymphoma (ATL) in the 1980s by researchers in both the United States and Japan. It was classified as the exclusive causative agent of ATL. HTLV-1 is a member of the deltaretrovirus family and has been established as the first retrovirus to directly be associated with human malignancy (cancer). It is estimated that 5-20 million people are infected with HTLV-1. HTLV-1 is endemic in southern Japan, parts of the Caribbean, most of Africa, South America, and is also be seen in a lower frequency over many other areas of the world. A commonality between HTLV-1 and other retroviruses is that it encodes a protease (PR) necessary for it to mature. In other retroviruses inhibition of the PR has shown to prevent the further spread of viral information. This makes the development of inhibitors specific to the HTLV-1 virus PR an attractive new direction for research. Compared to other retroviruses such as HIV, HTLV-1 has received very little attention with only a minimal literature occurrence. Building upon the work established by Aimoto and co-workers, Kenichi Akaji and co-workers were able to synthesize a protease inhibitor that successfully interacted with the Aimoto protease.The synthesis of the Akaji protease inhibitor was accomplished by the use of chiral auxiliary methodology combined with solid phase support chemistry to allow for the protection of a secondary alcohol and the addition of the tripeptide at the β-amino position.<b><i> </i></b>We recently became interested in the asymmetric synthesis of the protease inhibitor for the HTLV-1 using a glycolate aldol addition route. This poster will summarize the work that has been carried out on developing an efficient synthesis of the Akaji protease inhibitor. The summary will include the work that was accomplished with a variety of glycolate aldol additions directed by oxazolidine-2-thiones chiral auxiliaries. The aldol addition products that were obtained were reductively cleaved to generate the corresponding diol that was chemoselectively sulfonylated with toluenesulfonyl chloride. Treatment of this system with a variety of nucleophiles resulted in oxetane formation as the intermediate. The reactivity of the formed oxetane will be discussed as well as future plans for completing this body of work.

Efforts towards the formal asymmetric synthesis of the Akaji Human T-cell leukemia virus (HTLV-1) protease inhibitor

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.