Physical Sciences and Mathematics Commons^™

Design And Synthesis Of Handles For Solid-Phase Peptide Synthesis And Convergent Peptide Synthesis, Jose Giraldes

LSU Doctoral Dissertations

The recent popularity of methods for solid-phase peptide synthesis that use the 9-fluorenylmethyloxycarbonyl (Fmoc) group for N^α-amino protection has created a need for compatible anchoring linkages and handles. In an effort to develop mild new methods for use in solid-phase peptide synthesis (SPPS), a new ferrocene containing linker or “handle”, the 1’1-ferrocenyl carboxaldehyde handle was designed, synthesized, characterized and tested. This linker is analogous to those commercially available and developed by Barany. The ferrocenyl amine linker(FAL) releases C-terminal peptide amides upon acidolysis. Since the FAL handle is acid labile it is compatible with Fmoc and N^α-dithiasuccinoyl …