Synthesis 2020; 52(04): 537-543
DOI: 10.1055/s-0039-1690016
paper
© Georg Thieme Verlag Stuttgart · New York

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

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,
Vanesa López-Sobrado
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Departamento de Química, Facultade de Ciencias and Centro de Investigacións Científicas Avanzadas (CICA), Universidade da Coruña, 15071 A Coruña, Spain   Email: elena.pazos@udc.es
› Author Affiliations
This work has received financial support from the Ministerio de Economía y Competitividad and Fondo Europeo de Desarrollo Regional (FEDER) (CTQ2016-75629-P), Agencia Estatal de Investigación and FEDER (CTQ2017-89166-R), and the Consellería de Educación, Universidade e Formación Profesional, Xunta de Galicia (ED431C 2018/39).
Further Information

Publication History

Received: 29 May 2019

Accepted after revision: 16 July 2019

Publication Date:
30 July 2019 (online)


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.

Supporting Information

 
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