Title page for ETD etd-0407103-115838


Type of Document Dissertation
Author Giraldes, Jose
Author's Email Address jgiral1@lsu.edu
URN etd-0407103-115838
Title Design and Synthesis of Handles for Solid-Phase Peptide Synthesis and Convergent Peptide Synthesis
Degree Doctor of Philosophy (Ph.D.)
Department Chemistry
Advisory Committee
Advisor Name Title
Mark McLaughlin Committee Chair
Robert Strongin Committee Member
Steven Watkins Committee Member
William Crowe Committee Member
Ding Shih Dean's Representative
Keywords
  • ferrocenylamine
  • ferrocene
  • ferrocenyl
  • ligation
  • peptide
Date of Defense 2003-04-01
Availability unrestricted
Abstract
The recent popularity of methods for solid-phase peptide synthesis that use the 9-fluorenylmethyloxycarbonyl (Fmoc) group for Nα-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 Nα-dithiasuccinoyl (Dts) based chemistries, but not Nα-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.
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