Structural mimicry of two cytochrome b(562) interhelical loops using macrocycles constrained by oxazoles and thiazoles

Yogendra Singh; Martin J Stoermer; Andrew J Lucke; Tom Guthrie; David P Fairlie

doi:10.1021/ja0455300

Structural mimicry of two cytochrome b(562) interhelical loops using macrocycles constrained by oxazoles and thiazoles

J Am Chem Soc. 2005 May 11;127(18):6563-72. doi: 10.1021/ja0455300.

Authors

Yogendra Singh¹, Martin J Stoermer, Andrew J Lucke, Tom Guthrie, David P Fairlie

Affiliation

¹ Centre for Drug Design and Development, Institute for Molecular Bioscience, University of Queensland, Brisbane, Qld 4072, Australia.

PMID: 15869277
DOI: 10.1021/ja0455300

Abstract

A major chemical challenge is the structural mimicry of discontinuous protein surfaces brought into close proximity through polypeptide folding. We report the design, synthesis, and solution structure of a highly functionalized saddle-shaped macrocyclic scaffold, constrained by oxazoles and thiazoles, supporting two short peptide loops projecting orthogonally from the same face of the scaffold. This structural mimetic of two interhelical loops of cytochrome b(562) illustrates a promising approach to structurally mimicking discontinuous loops of proteins.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Biomimetic Materials / chemistry
Biomimetic Materials / metabolism
Cytochrome b Group / chemistry*
Cytochrome b Group / metabolism
Escherichia coli Proteins / chemistry*
Escherichia coli Proteins / metabolism
Macrocyclic Compounds / chemistry*
Macrocyclic Compounds / metabolism
Models, Molecular
Oxazoles / chemistry*
Protein Structure, Quaternary
Solutions
Surface Properties
Thiazoles / chemistry*

Substances

Cytochrome b Group
Escherichia coli Proteins
Macrocyclic Compounds
Oxazoles
Solutions
Thiazoles
cytochrome b562, E coli