Click Chemistry Peptides

Click chemistry, which is also translated as "link chemistry" and "fast mating combinatorial chemistry". It is a synthetic concept introduced by chemist Barry Sharpless (K B Sharpless) in 2001. The purpose is to quickly and reliably complete the chemical synthesis of all kinds of molecules through the splicing of small units. In particular, it emphasizes the development of new combinatorial chemistry methods based on carbon-heteroatom bond (C-X-C) synthesis, and with the help of these reactions to obtain molecular diversity simply and efficiently. Creative Peptides can help you achieve the goal of clicking chemical peptides quickly and effectively.

Advantage of Click chemistry

The click reaction has the advantages of high efficiency, wide range, stereospecific and easy to use cheap reagents. The technology has great potential to modify peptides and proteins, such as connecting ligands, lipophilic or hydrophobic groups, or hydrophilic and hydrophobic junctions. This reaction can be greatly accelerated in the discovery of new peptide drugs.

Application of Click Chemistry in Peptide

The simplicity and reliability of CuAAC, as well as the biological orthogonality of the initial reactants, have contributed to a wide range of peptide science applications. The most important applications of click chemistry in peptide science include cyclization, chemical bonding, and binding with biomolecules, nanoparticles, polymers and other chemical entities. Peptide modification using various applications of click chemistry can be carried out in different ways. For example, peptides can be converted into azide derivatives after synthesis, which can be clicked with an appropriate substrate containing clickable alkynyl groups, and vice versa. Peptides can also be prepared by intermolecular and intramolecular click reactions using azides or alkynes containing amino acids or structural units in the process of peptide synthesis.

To apply click chemistry in peptides, we need two steps: first, to introduce alkynyl groups into peptides according to structural needs; second, to introduce azide groups into peptides.

For example, introducing alkynyl or azide groups into the peptide Ala-Ala-Ala-Ala

• Introduction of alkynyl groups

Caproic acid modification

Pentynic acid modification

Propargyl glycine

DBCO ring, such as DBCO-PEG4,DBCO-Acid,DBCO-NHS

• Introduction of azide group

Introduction of azido acetic acid

Introduction of azidopentanoic acid

Introduction of azido caproic acid

Introduction of side chain azide Lys

Introduction of azide PEG6

Our Services

• Synthesize clickable amino acids to incorporate peptides.
• Synthesis of chemical structural unit of peptide click.
• Biological coupling, binding, binding peptides and macrocyclization.
• Synthesis of clickable peptides containing alkyne or azide functional groups.
• Binding with small molecules, PEG chains, surfaces, metal chelates, fluorophores and sugars.
• Design and synthesis of substituted cyclooctyne modified peptide for copper-free click reaction.
• Synthesis, conformation and skeleton modification of peptide mimics based on triazole skeleton.

References

1. Li, H., Aneja, R., & Chaiken, I. (2013). Click chemistry in peptide-based drug design. Molecules, 18(8), 9797-9817.
2. Ahmad Fuaad, A. A., Azmi, F., Skwarczynski, M., & Toth, I. (2013). Peptide conjugation via CuAAC ‘click’chemistry. Molecules, 18(11), 13148-13174.
3. Quigley, N. G., Tomassi, S., Di Leva, F. S., Di Maro, S., Richter, F., Steiger, K., ... & Notni, J. (2020). Click‐Chemistry (CuAAC) Trimerization of an αvβ6 Integrin Targeting Ga‐68‐Peptide: Enhanced Contrast for in‐Vivo PET Imaging of Human Lung Adenocarcinoma Xenografts. ChemBioChem, 21(19), 2836-2843.