Cyclic peptides and cyclic proteins are  useful tools in chemical biology and pharmaceutical science.

(1)Disulfide Bridges

Disulfide Bridges:offer the formation of cyclic peptides via disulfide bridges between cysteine residues within the peptide. We  can synthesize peptides containing up to 4 disulfide bonds by employing solid  phase peptide synthesis. Using the hydrazide-based ligation method, three  subfamilies (i.e. Mçbius, bracelet, and trypsin inhibitor) of cyclotides can  all be readily synthesized with high efficiencies. Our approach to the  synthesis of cyclotides involves three distinct stages: synthesis of linear  peptide hydrazide, ring-closing macrolactam formation by the hydrazide-based  ligation, and final oxidative folding to the native Cys-knot topology.

Scheme 1.Synthetic strategy for the preparation of three subfamilies of  cyclotides.

(2)Amide Cyclization

We developed a new peptide cyclization method on the basis of the hydrazide ligation. This new method provides an easier and less expensive means to prepare various cyclic peptides and cyclic proteins. Its major advantage is that peptide hydrazides can be easily prepared by using the routine use of Fmoc solid-phase peptide synthesis. Thus the present method can be used to synthesize various cyclic peptides and cyclic proteins with increased simplicity and lower costs. We have successfully synthesized various longer cyclic peptides (9–42 AA).

Scheme 2. Synthesis of cyclic peptides and cyclic proteins through the ligation of peptide hydrazides.

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