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