Review
Constraining Cyclic Peptides To Mimic Protein Structure Motifs
Dr. Timothy A. Hill,
Dr. Nicholas E. Shepherd,
Dr. Frederik Diness,
Prof. Dr. David P. Fairlie,
Dr. Timothy A. Hill
Division of Chemistry and Structural Biology, Institute for Molecular Bioscience, The University of Queensland, Brisbane, Queensland 4072 (Australia)
Search for more papers by this authorDr. Nicholas E. Shepherd
School of Molecular Biosciences, The University of Sydney, New South Wales 2006 (Australia)
Search for more papers by this authorDr. Frederik Diness
Center for Evolutionary Chemical Biology, Department of Chemistry, University of Copenhagen, Copenhagen (Denmark)
Search for more papers by this authorCorresponding Author
Prof. Dr. David P. Fairlie
Division of Chemistry and Structural Biology, Institute for Molecular Bioscience, The University of Queensland, Brisbane, Queensland 4072 (Australia)
Division of Chemistry and Structural Biology, Institute for Molecular Bioscience, The University of Queensland, Brisbane, Queensland 4072 (Australia)Search for more papers by this authorDr. Timothy A. Hill,
Dr. Nicholas E. Shepherd,
Dr. Frederik Diness,
Prof. Dr. David P. Fairlie,
Dr. Timothy A. Hill
Division of Chemistry and Structural Biology, Institute for Molecular Bioscience, The University of Queensland, Brisbane, Queensland 4072 (Australia)
Search for more papers by this authorDr. Nicholas E. Shepherd
School of Molecular Biosciences, The University of Sydney, New South Wales 2006 (Australia)
Search for more papers by this authorDr. Frederik Diness
Center for Evolutionary Chemical Biology, Department of Chemistry, University of Copenhagen, Copenhagen (Denmark)
Search for more papers by this authorCorresponding Author
Prof. Dr. David P. Fairlie
Division of Chemistry and Structural Biology, Institute for Molecular Bioscience, The University of Queensland, Brisbane, Queensland 4072 (Australia)
Division of Chemistry and Structural Biology, Institute for Molecular Bioscience, The University of Queensland, Brisbane, Queensland 4072 (Australia)Search for more papers by this authorGraphical Abstract
Short peptides can be constrained by cyclization to recreate key folded elements of protein structure, like β-strands and β-sheets, α-helices, and turn motifs. Coupled with internal molecular constraints, cyclization has led to many protease-resistant, potent and target-selective, biologically active compounds for use in biology and medicine.
Abstract
Many proteins exert their biological activities through small exposed surface regions called epitopes that are folded peptides of well-defined three-dimensional structures. Short synthetic peptide sequences corresponding to these bioactive protein surfaces do not form thermodynamically stable protein-like structures in water. However, short peptides can be induced to fold into protein-like bioactive conformations (strands, helices, turns) by cyclization, in conjunction with the use of other molecular constraints, that helps to fine-tune three-dimensional structure. Such constrained cyclic peptides can have protein-like biological activities and potencies, enabling their uses as biological probes and leads to therapeutics, diagnostics and vaccines. This Review highlights examples of cyclic peptides that mimic three-dimensional structures of strand, turn or helical segments of peptides and proteins, and identifies some additional restraints incorporated into natural product cyclic peptides and synthetic macrocyclic peptidomimetics that refine peptide structure and confer biological properties.
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