2, 2′-Bipyridine and hydrazide containing peptides for cyclization and complex quaternary structural control. (23rd April 2018)

• Record Type: Journal Article
• Authors: Hernandez, Erik T.; Escamilla, P. Rogelio; Kwon, Sang-Yop; Partridge, Jonathan; McVeigh, Matthew; Rivera, Sebastian; Reuther, James F.; Anslyn, Eric V.
• Is Part Of: New journal of chemistry. Volume 42:Number 11(2018)
• Page Start: 8577
• Page End: 8582
• Publication Date: 2018-04-23
• Subjects: Chemistry -- Periodicals; Chimie -- Périodiques; 540
• DOI: 10.1039/c8nj00184g
• Languages: English
• ISSNs: 1144-0546

Abstract

Abstract : Complex quaternary structure formation of bipy peptide ligands. Abstract : A synthetic peptide containing two N ε -methyl lysines (Ac-K( N ε -Me)GYTGYTGK( N ε -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 ε -Me, N ε -Bipy)GYTGYTGK( N ε -Me, N ε -Bipy)D-OH. Peptides with a bipyridine at the 6-position did not bind to Fe 2+ and Zn 2+ . 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.