Synthesis and chemical reactivity of thiophenoxyphenylalanine bioisosteres, suitable synthons for the design of HIV protease inhibitors

Abstract

Phenylalanine in which the methylene group is replaced by a sulfur atom could be a useful bioisostere for the design of HIV-protease inhibitors. Due to the chemical instability of hemiaminal intermediates, these bioisosteres have to be prepared from α-hydroxyglycine following specific synthetic routes. In this paper, we report the synthesis of sulfenylated phenylalanine bioisosteres 2 and 3, which represent two original building-blocks for peptide solid phase synthesis.