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Issue 11, 2018
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2,2′-Bipyridine and hydrazide containing peptides for cyclization and complex quaternary structural control

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Abstract

A synthetic peptide containing two Nε-methyl lysines (Ac-K(Nε-Me)GYTGYTGK(Nε-Me)D-OH) was alkylated with bipyridine (bipy) ligands substituted at the fifth (MP-5) and sixth (MP-6) positions, thereby creating Ac-K(Nε-Me, Nε-Bipy)GYTGYTGK(Nε-Me, Nε-Bipy)D-OH. Peptides with a bipyridine at the 6-position did not bind to Fe2+ and Zn2+. Peptides with a bipyridine at the 5-position bound these metals, and in the presence of one equivalent of a free bipy derivative folded into a macrocycle. Further, the free bipy derivative could also contain a cyclized peptide derived from hydrazone formation, resulting in a complex but controlled quaternary peptide structure.

Graphical abstract: 2,2′-Bipyridine and hydrazide containing peptides for cyclization and complex quaternary structural control

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Supplementary files

Article information


Submitted
11 Jan 2018
Accepted
11 Apr 2018
First published
11 Apr 2018

New J. Chem., 2018,42, 8577-8582
Article type
Paper
Author version available

2,2′-Bipyridine and hydrazide containing peptides for cyclization and complex quaternary structural control

E. T. Hernandez, P. R. Escamilla, S. Kwon, J. Partridge, M. McVeigh, S. Rivera, J. F. Reuther and E. V. Anslyn, New J. Chem., 2018, 42, 8577
DOI: 10.1039/C8NJ00184G

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