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

Published as part of the Bürgenstock Special Section 2019 Future Stars in Organic Chemistry

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.

Key words

peptide-based conjugates - viologens - Zincke reaction - solid phase peptide synthesis (SPPS) - synthetic methodology

• References

• 1 Both authors contributed equally to this work.
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