Design and synthesis of handles for solid-phase peptide synthesis and convergent peptide synthesis

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 (Dts) based chemistries, but not N^α-tert-butyloxycarbonyl (Boc) based chemistries. The solid-phase linkage was investigated based on the stability of the ferrocenium ion. The stability of this ion is greater than that of the benzyl cations that are used in the handles developed previously.

Name thesis:degree_name

Doctor of Philosophy (PhD)

Level thesis:degree_level

Dissertation

Discipline thesis:degree_discipline

Chemistry

Grantor

Chemistry

Year dc:date.available

2003

Author dc:creator

• Giraldes, Jose

• ferrocenylamine
• ferrocene
• ferrocenyl
• ligation
• peptide

Statement dc:rights

• unrestricted
• Release the entire work immediately for access worldwide.

Identifier

etd-0407103-115838
https://repository.lsu.edu/gradschool_dissertations/1146

OAI identifier oai:identifier

oai:repository.lsu.edu:gradschool_dissertations-2145