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

Abstract

A synthetic peptide containing two N-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 6-position bipyridine did not bind to Fe2+ and Zn2+. Peptides with 5-position bipyridine 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 complex but controlled quaternary peptide structure.

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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, Accepted Manuscript
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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. A. Kwon, J. Partridge, M. McVeigh, S. Rivera, J. F. Reuther and E. V. Anslyn, New J. Chem., 2018, Accepted Manuscript , DOI: 10.1039/C8NJ00184G

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