Solid-Phase Zincke Reaction for the Synthesis of Peptide-4,4′-bipyridinium Conjugates

Abstract

We present herein the development of a new synthetic strategy for the conjugation of 4,4′-bipyridinium derivatives into peptide scaffolds. The methodology, based on the development of a solid-phase version of the Zincke reaction between activated pyridinium salts and amines, is able to produce the desired conjugates in a straightforward fashion, with the bipyridinium units attached at the N-terminus of peptides or at Lys side chains of N-terminal acetylated peptides.

Controlled Formation of Emissive Gold Nanoclusters with a Synthetic Self-Assembled Protein Toroid

“…The small size of the gp23.1 monomer puts it within the reach of standard solid-phase peptide synthesis methods, which allow the straightforward preparation of new sequences, including those containing artificial functionalities, as well as the implementation of powerful postsynthetic modifications. [18][19][20][21] This synthetic availability combined with the predictable oligomerization of these chemically synthesized monomers, makes of gp23.1 a potentially valuable platform for bottom-up nanotechnological applications. [22][23][24][25][26]…”

Reversible Control of DNA Binding with Cucurbit[8]uril-Induced Supramolecular 4,4′-Bipyridinium–Peptide Dimers

“…For the coupling of the 4,4′-bipyridinium unit 1 to the orthogonally deprotected C-terminal Lys side chain, we followed our previously reported methodology based on a solid-phase Zincke reaction (Schemes S1 and S2). 35 In addition to P1, we also synthesized its methylated counterpart P2 and P3, a peptide that lacks the 4,4′-bipyridinium moiety, as negative controls of the DNA binding, and the disulfide dimer of GCN4br, P4 2 , 25 as positive control (Figure 1a and Schemes S1, S2, S3, and S4). With P1 at hand, we studied its binding to CB [8] by UV spectroscopy.…”