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Creative Peptides provides a wide range of cyclic peptide synthesis, which play a key role in different processes and have good therapeutic potential because they have several favorable properties, such as displaying a large surface area, which leads to high affinity and selectivity for protein targets, as well as their limited conformational flexibility, reducing entropy penalties during binding, thus improving their binding performance.
Depending on the cyclization position, there are several methods to synthesize cyclic peptides: head-to-tail, side-chain-to-side-chain, head-to-side-chain, and side-chain-to-tail, head-to-backbone, backbone-to-tail, side-chain-to-backbone, backbone-to-side-chain. (see figure below). While head-to-tail cycles are usually formed by amide bond formation, side-chain-to-side-chain cycles are most often synthesized via Cys-Cys or amide bond formation.
Backbone cyclic peptides are easily assembled via the formation of an amide bond between the peptides own N-terminus amine and C-terminus carboxylic acid. Our commonly used methods are chemical synthesis and biosynthesis. Creative Peptides perform the reaction with very high yields, and routinely provide over 98% purified cycled peptides.
Side chain-to-side chain cyclization is frequently employed to stabilize and select specific conformations and to reduce susceptibility toward proteolytic degradation. Creative Peptides have the capable to selectively protect, and then deprotect peptide sidechains to allow for the formation of lactam bridges between Lysine or Diaminopropanoic acid, and Glutamic and Aspartic Acids. Creative Peptides can even perform multiple different sites for bridge formation.
Disulfide bonds are widely present in hormones, enzymes, and immunoglobulins, and are thought to play an important role in reconstructing the conformation of biologically active peptides. To further enhance biological activity, people often introduce disulfide bonds to modify bioactive peptides. Creative Peptides usually add two cysteine residues to the peptide sequence, and the dilute solution of the peptide undergoes mild oxidation to form the desired intramolecular disulfide bond between the two cysteine residues. Ugi reaction also can be provided.
Disulfide bonds can be easily reduced to their acyclic mercaptan form in the intracellular environment. This challenge can be overcome by hydrocarbon-bound peptide synthesis, which can form a stable α-helix structure. It can mimic the typical molecular structure at the protein-protein interaction interface. When locked in this stable configuration, the constrained peptides can penetrate the cell and act on the protein targets in the cell.
Creative Peptides has successfully synthesized the target molecules needed by customers through SSPS.
Fig. 3 Typical synthesis case
Reference
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