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Published on: May 15, 2012
Protection of the Hydroxyphosphinyl Function of Phosphinic Dipeptides by Adamantyl. Application to the Solid-Phase
Athanasios Yiotakis1, Stamatia Vassiliou, Jirí Jirácek
1Department of Organic Chemistry, Laboratory of Organic Chemistry, University of Athens, Panepistiomiopolis, Zografou, Athens, 15771, Greece, and Département d'Ingénierie et d'Etudes des Protéines, CEA-Direction des Sciences du Vivant, Centre d'Etudes de Saclay, 91191 Gif/Yvette Cedex, France.
Abstract:
To develop solid-phase synthesis of phosphinic peptides, different FmocXaaPsi{PO(OAd)CH(2)}XaaOH building blocks have been prepared, where Fmoc is (fluorenylmethoxy)carbonyl. In this respect, the protection of the hydroxyphosphinyl function in these phosphinic dipeptides by the adamantyl group turns out to be convenient. The phosphinic adamantyl esters are completely stable in basic conditions and can be removed under relatively mild acidic conditions. Using these building blocks, despite the bulkiness of the adamantyl group, no particular problem of coupling was observed during the solid-phase synthesis of phosphinic peptides by the Fmoc strategy. The developed methodology is of particular interest to facilitate the development of potent inhibitors of zinc-metalloproteases.
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