Wang Resin: Acid-Labile Solid Support for Peptide Synthesis
Wang Resin is a polystyrene-based solid-phase resin functionalized with a Wang linker (4-hydroxymethylphenoxy), used extensively in Fmoc and Boc solid-phase peptide synthesis (SPPS). It is primarily employed when a C-terminal carboxylic acid (-COOH) is desired in the final peptide product.
Developed by Samuel J. Wang, this resin has become a cornerstone in peptide chemistry due to its acid-labile ester linkage, reliable cleavage, and broad solvent compatibility.
Key Features
Matrix: Cross-linked polystyrene (typically 1% DVB)
Linker: Wang (acid-labile, forms ester bond with first amino acid)
Functional Group: Hydroxyl (-OH)
Loading: Typically 0.8–1.2 mmol/g
Compatible Chemistries: Fmoc and Boc protocols
Cleavage Conditions: Cleaved under TFA (trifluoroacetic acid), releasing peptide with C-terminal -COOH
Applications
Peptide synthesis with C-terminal acid functionality
Solid-phase organic synthesis (SPOS)
Combinatorial chemistry for drug discovery
Immobilization of intermediates or building blocks
Advantages
Clean, high-yield acid cleavage
Versatile and widely applicable
Commercially available in various mesh sizes and loading levels
Compatible with both manual and automated synthesizers
Storage and Handling
Store dry, away from light and moisture
Swell in appropriate solvents (e.g., DCM, DMF) before use
Handle under inert atmosphere if storing for long periods
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