Chemoselective protection of solid-phase compatible Fmoc-phosphinic building blocks |
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| Authors: | Nasopoulou Magdalini Matziari Magdalini Dive Vincent Yiotakis Athanasios |
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| Institution: | University of Athens, Department of Chemistry, Laboratory of Organic Chemistry, Panepistimiopolis Zografou 15771, Athens, Greece. |
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| Abstract: | An efficient four-step synthetic strategy able to fully discriminate hydroxyphosphinyl and carboxylic groups of Fmoc-phosphinic building blocks and related analogues has been developed. The proposed method applies selective acidic removal of the phenacyl (Pac) group from the hydroxyphosphinyl functionality and protection by the 1-adamantyl (Ad) group. Reductive removal of the Pac group from the carboxylic functionality leads to Fmoc-protected phosphinic pseudodipeptidic units suitable for phosphinic peptide and library development using solid-phase peptide synthesis (SPPS). |
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