Wang Resin

Definition

Wang resin is a type of solid support material commonly used in peptide synthesis, particularly in the Merrifield solid-phase method. It is a polymeric resin that serves as a platform for the stepwise assembly of peptide chains.

5 Must Know Facts For Your Next Test

1. Wang resin is a hydroxymethyl polystyrene-based resin that is functionalized with a linker molecule, typically a benzyl ester or an acid-labile linker.
2. The linker on Wang resin allows the synthesized peptide to be cleaved from the resin using mild acid conditions, preserving the peptide's structure and functionality.
3. Wang resin is commonly used in the Merrifield solid-phase peptide synthesis method, which involves the stepwise addition of protected amino acids to the growing peptide chain on the solid support.
4. The use of Wang resin in SPPS enables the rapid and efficient synthesis of peptides by allowing for easy purification and automation of the process.
5. The loading capacity and swelling properties of Wang resin make it a versatile and widely-used solid support for the synthesis of a variety of peptides and related compounds.

Review Questions

• Explain the role of Wang resin in the Merrifield solid-phase peptide synthesis method.
  • In the Merrifield solid-phase peptide synthesis method, Wang resin serves as the solid support on which the peptide chain is assembled. The resin is functionalized with a linker molecule that allows the synthesized peptide to be cleaved from the support under mild acid conditions, preserving the peptide's structure and functionality. The use of Wang resin enables the rapid and efficient synthesis of peptides by facilitating easy purification and automation of the process.
• Describe the key features of Wang resin that make it a suitable solid support for peptide synthesis.
  • Wang resin is a hydroxymethyl polystyrene-based resin that is functionalized with a linker molecule, typically a benzyl ester or an acid-labile linker. This linker allows the synthesized peptide to be cleaved from the resin using mild acid conditions, preserving the peptide's structure and functionality. Additionally, the loading capacity and swelling properties of Wang resin make it a versatile and widely-used solid support for the synthesis of a variety of peptides and related compounds, as it enables the rapid and efficient assembly of peptide chains through the Merrifield solid-phase method.
• Analyze the advantages of using Wang resin in the context of automated peptide synthesis compared to other solid supports.
  • The use of Wang resin in automated peptide synthesis, such as the Merrifield solid-phase method, offers several advantages over other solid supports. Firstly, the linker on Wang resin allows the synthesized peptide to be cleaved from the resin using mild acid conditions, preserving the peptide's structure and functionality. This is crucial for maintaining the integrity of the final product. Additionally, the loading capacity and swelling properties of Wang resin enable the rapid and efficient assembly of peptide chains, facilitating the automation of the synthesis process. Furthermore, the ease of purification afforded by the solid-phase approach, combined with the versatility of Wang resin, make it a widely-used and preferred solid support for the synthesis of a diverse range of peptides and related compounds.

Related terms

Solid-Phase Peptide Synthesis (SPPS): A method of peptide synthesis where the growing peptide chain is attached to an insoluble polymeric support, allowing for easy purification and automation of the synthesis process.

Merrifield Solid-Phase Method: An automated peptide synthesis technique developed by Robert Merrifield, where the peptide is assembled on a solid support like Wang resin rather than in solution.

Linker: A chemical group that connects the first amino acid of the peptide to the solid support, allowing the peptide to be cleaved from the resin after synthesis.