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Differential Effects of ?3 - versus ?2 -Amino Acid Residues on the Helicity and Recognition Properties of Bim BH3-Derived ?/?-Peptides.

ABSTRACT: Oligomers containing ?- and ?-amino acid residues (?/?-peptides) have been shown to mimic the ?-helical conformation of conventional peptides when the unnatural residues are derived from ?3 -amino acids or cyclic ?-amino acids, but the impact of incorporating ?2 residues has received little attention. The effects of ?2 residues on the conformation and recognition behavior of ?/?-peptides that mimic an isolated ?-helix were investigated. This effort has focused on 26-mers based on the Bim BH3 domain; a set of isomers with identical ?/? backbones that differ only in the placement of certain side chains along the backbone (?3 vs. ?2 substitution) was compared. Circular dichroism data suggest that ?2 residues can be helix-destabilizing relative to ?3 residues, although the size of this effect seems to depend on side chain identity. Binding data show that ?3 ??2 substitution at sites that contact a partner protein, Bcl-xL , can influence affinity in a way that transcends effects on helicity.

SUBMITTER: Eddinger GA 

PROVIDER: S-EPMC6330212 | biostudies-literature | 2018 Oct

REPOSITORIES: biostudies-literature

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Differential Effects of β<sup>3</sup> - versus β<sup>2</sup> -Amino Acid Residues on the Helicity and Recognition Properties of Bim BH3-Derived α/β-Peptides.

Eddinger Geoffrey A GA   Gellman Samuel H SH  

Angewandte Chemie (International ed. in English) 20180920 42

Oligomers containing α- and β-amino acid residues (α/β-peptides) have been shown to mimic the α-helical conformation of conventional peptides when the unnatural residues are derived from β<sup>3</sup> -amino acids or cyclic β-amino acids, but the impact of incorporating β<sup>2</sup> residues has received little attention. The effects of β<sup>2</sup> residues on the conformation and recognition behavior of α/β-peptides that mimic an isolated α-helix were investigated. This effort has focused on  ...[more]

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