Peptoid Synthesis
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Peptoid Synthesis

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Peptoids, or poly-N-substituted glycines, are a class of peptidomimetics whose side chains are appended to the nitrogen atom of the peptide backbone, rather than to the α-carbons (as they are in amino acids). Notably, peptoids lack the amide hydrogen which is responsible for many of the secondary structure elements in peptides and proteins. Peptoids were first invented by Reyna J. Simon, Paul Bartlett and Daniel V. Santi to mimic protein/peptide products to aid in the discovery of protease-stable small molecule drugs.

Fig.1 Structural comparison between peptide and peptoid

Applications

• Screening a combinatorial library of diverse peptoids which yielded novel high-affinity ligands for 7-transmembrane G-protein-couple receptors.
• Antimicrobial agents.
• Synthetic lung surfactants.
• Ligands for various proteins including Src Homology 3 (SH3 domain), Vascular Endothelial Growth Factor (VEGF) receptor 2, and antibody Immunoglobulin G biomarkers for the identification of Alzheimer's disease.

Synthesis of peptoid

• Solid-Phase Synthesis
The first oligopeptoids reported were synthesized by solid-phase synthesis, for which a set of Fmoc-protected peptoid monomers was made. There are several advantages to this method, but the extensive synthetic effort required to prepare a suitable set of chemically diverse monomers is a significant disadvantage of this approach. Additionally, the secondary N-terminal amine in peptoid oligomers is more sterically hindered than the primary amine of an amino acid, which slows coupling reactions.

• Sub-monomer Solid-Phase Method
A major breakthrough came in 1992 when a much more efficient method of peptoid synthesis was invented. In this method, each N-substituted glycine (NSG) monomer is assembled from two readily available “sub-monomers” in the course of extending the NSG oligomer, this method is known as the sub-monomer method, in which each cycle of monomer addition consists of two steps, an acylation step and a nucleophilic displacement step.

• Side Reactions
There are a few competing side reactions that are unique to the synthesis of peptoid oligomers. For example, peptoid dimer synthesis often leads to formation of the cyclic diketopiperazines instead of the linear molecule. Sub-monomer whose side chains bear a nucleophile three of four atoms from the amino nitrogen, are also prone to cyclization after bromoacetylation.

Our services

Creative Peptides has developed an innovative peptoid synthesis service to meet the increasing needs in drug target discovery and lead structure discovery research, providing a confidential and efficient service at competitive prices.

Below is a list of our available peptoid side chain (include but not limited to the following):

Fig. 2 Our available peptoid side chain

References:
1. Simon, R. J., Kania, R. S., Zuckermann, R. N., Huebner, V. D., Jewell, D. A., Banville, S & Marlowe, C. K. (1992). Peptoids: a modular approach to drug discovery. Proceedings of the National Academy of Sciences, 89(20), 9367-9371.
2. Zuckermann, R. N. (2011). Peptoid origins. Peptide Science, 96(5), 545-555.
3. Vollrath, S. B., Fürniss, D., Schepers, U., & Bräse, S. (2013). Amphiphilic peptoid transporters–synthesis and evaluation. Organic & biomolecular chemistry, 11(47), 8197-8201.

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