Designer Peptides: Attempt to Control Peptide Structure by Exploiting Ferrocene as a Scaffold

Abstract

The design of peptides that display a β‐sheet‐like secondary structure remains a challenge. Molecular scaffolds, such as ferrocene (Fc) can help to overcome some of these challenges. Monosubstituted Fc derivatives offer no control over the self‐assembly of the conjugates, and the formation of supramolecular structures is entirely serendipitous. 1,n′‐disubstituted Fc derivatives provide a significant level of control over the direction of the peptide, their relative orientation, and the intramolecular hydrogen‐bonding patterns, which increases the rigidity of the molecule and in many cases, generates a new H‐bonding interface for intermolecular assembly. In this Microreview, we explore the use of ferrocene as a scaffold in the design of structurally well‐defined peptide conjugates. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

Hydrogen-bonding interactions in ferrocene-peptide conjugates containing valine

“…Other bands observed between 300 and 420 nm are characteristic of metal-centered transitions. The CD spectral patterns for all conjugates correlate nicely with results reported for other Fc-peptide conjugates possessing a "Herrick conformation" [29,30].…”

Elucidation of the Conformational Freedom of Ferrocene Amino Acid (Bio)Conjugates: A Complementary Theoretical and Experimental Approach

“…motif), respectively. These combined experimental and theoretical studies form a solid basis for the implementation of designer peptides using ferrocene as a scaffold [34], and also for the exploitation of conformational responses to external stimuli, for example, the attachment/detachment of charges using anions, protons or electrons in peptide-based smart materials [35].…”

The Outer-Coordination Sphere: Incorporating Amino Acids and Peptides as Ligands for Homogeneous Catalysts to Mimic Enzyme Function

“…Sandwich complexes also provide a direct synthetic route for incorporating amino acids since many derivatives of ferrocene or other metallo-sandwich complexes to which amino acids can easily be coupled are commercially available. Work in the groups of Rapic, Hirao, and Metzler-Nolte have extensively studied these catalysts and some of this work has been reviewed recently (161)(162)(163). However, because of its impact on understanding the outer-coordination Downloaded by [Fondren Library, Rice University ] at 12: 12 12 October 2012 sphere, this review would not be complete without some discussion of this research area.…”