Bipyridine ligand incorporation by alkylation and hydrazine formation: straightforward methodologies for cyclizing synthetic peptides about a metal center

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2017

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Kwon, Sang-Yop

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Abstract

Unnatural binding of peptides to metal centers were facilitated using covalent linkage methods. First, two model peptides MP-5 and MP-6 were alkylated with bipyridine ligands to methylated lysine side chains to introduce two unnatural side chains. Synthetic peptide HydPep had two hydrazide groups that condensed onto the aldehydes of 2,2'-bipyridine-4,4'-dicarbaldehyde to form a cyclic structure. MP-5 was successfully complexed about Fe2+ and Zn2+ metal centers with free bipyridines in a 1:1:1 ratio of peptide : bipyridine : metal. MP-5 was successfully complexed about a Fe2+ metal center with cyclic HydPep. MP-6 did not show any binding to metal centers due to steric hindrances.

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