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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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Publication details

The article was received on 11 Jan 2018, accepted on 11 Apr 2018 and first published on 11 Apr 2018


Article type: Paper
DOI: 10.1039/C8NJ00184G
Citation: New J. Chem., 2018,42, 8577-8582
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    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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