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• W1507719702 abstract "Previous research within the Curran group has demonstrated that ferrocene may be used as an organometallic constraint to induce the formation of α-helices in short peptides which traditionally possess undefined conformations. Through strategic placement of lysine residues at the i and i+3 positions within the peptide, such a constraint was accomplished via the crosslinking of the lysine side chains to ferrocene dicarboxylic acid chloride in solution phase synthesis. The aim of this work was to develop a method for solid phase peptide synthesis (SPPS) for the synthesis of these ferroceneconstrained helices. In particular, we seek to develop a method in which the nascent peptide can be cyclized while it is still anchored to the resin. For the synthesis, Fmoc-protected amino acids were utilized to afford the pentapeptide Ac-Lys(Aloc)-Ala-Val-Lys(Aloc)-Gly-NH2. For the synthesis, Fmoc-protected amino acids and Aloc side chain protecting groups were utilized due to the mild conditions under which they are removed. This allowed the use of a Rink Amide AM resin, which is cleaved under acidic conditions. In this study it was found that on resin Pd 0 catalyzed Aloc removal required very specific conditions and work up for efficient deprotection. Additionally, Fmoc-protected amino acids were utilized in an analogous manner to afford the pentapeptide Ac-Lys(Z)-Ala-Val-Lys(Z)-Gly-NH2 . The Z-protected pentapeptide was then removed from the resin, hydrogenated using Pd on C and subsequently cyclized with 1,1’-ferrocenedicarboxylix acid chloride. Results from on-resin cyclization indicate that a new approach must be developed in order to accomplish on-resin cyclization. Future work includes the use of different resins, different protecting groups, and different removal conditions for optimization. In solution phase, the ferrocene coupling, the data indicates that a peptide dimer with a single ferrocene was formed due to incomplete Z protecting group removal. Future work in solution phase includes hydrogenation and cyclization optimization." @default.
• W1507719702 created "2016-06-24" @default.
• W1507719702 creator A5077570007 @default.
• W1507719702 date "2012-01-01" @default.
• W1507719702 modified "2023-09-25" @default.
• W1507719702 title "Ferrocene Constrained Helical Peptides via On-Resin Cyclization" @default.
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