Peptide Hall of Fame

BOBTIDE (Son of Chadtide)

Designer:
Robert Hughes

Structure:
Bobtide

Sequence:
Ac-RWVEVNGOKMe3ILQ-NH2

Characteristics:

Bobtide is the derivative of Chadtide in which Lys9 is trimethylated. Bobtide was studied to investigate the effect of Lys methylation on cation-pi interactions as a mimic for the biological recognition of KMe3 in histone 3 by the protein chromodomain, in which KMe3 is bound in an aromatic cage. The histone 3-chromodomain interaction is known to result in gene silencing. Mutants of Bobtide were also studied to determine the role of aromatic interactions on Arg methylation and Lys acylation.

References:

R. M. Hughes, M. L. Waters*, "Influence of N-Methylation on a Cation-π Interaction Produces a Remarkably Stable β-Hairpin Peptide", J. Am. Chem. Soc., 2005, 127, 6518-9.

R. M. Hughes, M. L. Waters*,"Arginine Methylation in a β-Hairpin Peptide: Implications for Arg-π Interactions, DCp°, and the Cold Denatured State", J. Am. Chem. Soc., 2006, 128, 12735-12742.

R. M. Hughes, M. L. Waters*, "Effects of Lysine Acylation in a β-Hairpin Peptide: Comparison of an Amide-π and a Cation-π Interaction", J. Am. Chem. Soc., 2006, 128, 13586-13591.

R. M. Hughes, K. R. Wiggins, S. Khorasanizadeh, M. L. Waters*, "Molecular Recognition of Trimethyllysine by Chromodomain Is Not Just the Hydrophobic Effect", Proc. Natl. Acad. Sci., USA, 2007, 104, 11184-11188.