title: Chemoselective protection of solid-phase compatible Fmoc-phosphinic building blocks.
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).
authors.affiliation: University of Athens, Department of Chemistry, Laboratory of Organic Chemistry, Panepistimiopolis Zografou 15771, Athens, Greece.
authors.forename: Magdalini
authors.initials: M
authors.lastname: Nasopoulou
authors.forename: Magdalini
authors.initials: M
authors.lastname: Matziari
authors.forename: Vincent
authors.initials: V
authors.lastname: Dive
authors.forename: Athanasios
authors.initials: A
authors.lastname: Yiotakis
mesh_terms: D009682:Magnetic Resonance Spectroscopy; D010721:Phosphinic Acids / Q000737:chemistry*; D021241:Spectrometry, Mass, Electrospray Ionization
chemical_list: D010721:Phosphinic Acids