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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(N?-Me)GYTGYTGK(N?-Me)D-OH) was alkylated with bipyridine (bipy) ligands substituted at the fifth (MP-5) and sixth (MP-6) positions, thereby creating Ac-K(N?-Me, N?-Bipy)GYTGYTGK(N?-Me, N?-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.

SUBMITTER: Hernandez ET 

PROVIDER: S-EPMC6205519 | biostudies-literature | 2018 Jun

REPOSITORIES: biostudies-literature

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

Hernandez Erik T ET   Rogelio Escamilla P P   Kwon Sang-Yop SY   Partridge Jonathan J   McVeigh Matthew M   Rivera Sebastian S   Reuther James F JF   Anslyn Eric V EV  

New journal of chemistry = Nouveau journal de chimie 20180411 11

A synthetic peptide containing two N<sub>ε</sub>-methyl lysines (Ac-K(N<sub>ε</sub>-Me)GYTGYTGK(N<sub>ε</sub>-Me)D-OH) was alkylated with bipyridine (bipy) ligands substituted at the fifth (<b>MP-5</b>) and sixth (<b>MP-6</b>) positions, thereby creating Ac-K(N<sub>ε</sub>-Me, N<sub>ε</sub>-Bipy)GYTGYTGK(N<sub>ε</sub>-Me, N<sub>ε</sub>-Bipy)D-OH. Peptides with 6-position bipyridine did not bind to Fe<sup>2+</sup> and Zn<sup>2+</sup>. Peptides with 5-position bipyridine bound these metals, and in  ...[more]

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