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Lewis acid-nitromethane complex-promoted Friedel-Crafts reactions of PS-DVB-resins
Authors:Christos Zikos  George Alexiou
Affiliation:a Laboratory of Organic Chemistry, Chemistry Department, University of Athens, 157 71, Greece
b Laboratory of Immunopeptide Chemistry IRRP, National Centre for Scientific Research ‘Demokritos’, Athens 153 10, Greece
c Biomedica Life Sciences S.A., Athens 152 32, Greece
Abstract:Aminomethyl-polystyrene resins were prepared using FeCl3-nitromethane and FeCl3-benzophenone complexes as Friedel-Crafts catalysts. All the resins were highly loaded and functionalized with Rink amide linker. A comparative synthesis of the classic difficult sequence ACP (65-74) on the prepared resins by Fmoc/t-Bu chemistry is presented. The target peptide of highest purity (91%) was that prepared using FeCl3-nitromethane.
Keywords:Friedel-Crafts alkylation   Solid-phase synthesis   Peptides
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