Hydroxylamine Wang Resin: Specialized Resin for Peptide Hydrazide and Hydroxamic Acid Synthesis
Hydroxylamine Wang Resin is a modified polystyrene-based resin functionalized with a Wang linker bearing a hydroxylamine (-NH–OH) functional group. This resin is designed for solid-phase synthesis of peptide hydroxamic acids, peptide hydrazides, and other bioactive molecules that require a C-terminal hydroxamic acid or hydroxylamine derivative.
The resin combines the well-known acid-labile Wang linker with a hydroxylamine moiety, allowing for Fmoc-compatible peptide synthesis and efficient cleavage under mild acidic conditions (e.g., TFA), yielding the final product with a hydroxamic acid or hydroxylamine C-terminus.
Specifications
Matrix: Polystyrene cross-linked with ~1% DVB
Linker: Wang-type (acid-labile)
Functional Group: Hydroxylamine (–NH–OH)
Loading: Typically 0.3–0.8 mmol/g
Particle Size: 100–200 mesh (75–150 µm)
Compatible Chemistry: Fmoc/tBu solid-phase peptide synthesis
Cleavage: TFA-based acidic cleavage
Final Product: Peptides with C-terminal hydroxamic acid or hydroxylamine derivatives
Key Features
Fmoc-Compatible: Seamless integration with standard SPPS protocols
C-Terminal Hydroxamic Acids: Enables synthesis of metalloprotease inhibitors and bioisosteres
Hydrazide/Hydroxamate Derivatives: Useful intermediates in peptide thioester or ligation chemistry
Mild Cleavage Conditions: TFA cleavage yields products with minimal side reactions
High Purity: Clean release of final product, ideal for therapeutic and diagnostic applications
Applications
Synthesis of peptide hydroxamic acids (e.g., HDAC inhibitors, MMP inhibitors)
Peptide hydrazide precursors for native chemical ligation (NCL)
Hydroxamate-containing drug candidates
Custom peptide building blocks
Solid-phase organic synthesis (SPOS) involving nucleophilic nitrogen end groups
Cleavage & Deprotection
Cleavage Reagent: 95% TFA + scavengers (e.g., TIS, water)
Cleavage Time: 1–2 hours at room temperature
Result: C-terminal hydroxamic acid or hydroxylamine derivative, depending on synthesis route
Handling & Storage
Store dry, under inert gas (argon or nitrogen), and away from light and moisture
Swell in DCM or DMF prior to use
Compatible with automated and manual peptide synthesizers
Avoid extended exposure to strong bases, which may degrade hydroxylamine functionality
Comparison with Related Resins
| Resin | Terminal Functional Group | Cleavage Method | Application |
|---|---|---|---|
| Hydroxylamine Wang | Hydroxamic acid / NH–OH | TFA | HDAC/MMP inhibitors, hydrazide synthesis |
| Rink Amide Resin | Amide (–CONH₂) | TFA | C-terminal amide peptides |
| Wang Resin | Carboxylic acid (–COOH) | TFA | Standard peptides with free acid |
| Hydrazine Resin | Hydrazide (–CONHNH₂) | TFA | Ligation precursors |
Conclusion
Hydroxylamine Wang Resin is a versatile and reliable solid-phase support for the synthesis of C-terminally modified peptides including hydroxamic acids, peptide hydrazides, and related analogs. Its compatibility with Fmoc chemistry and mild acid cleavage make it an essential resin for developing bioactive peptide therapeutics, enzyme inhibitors, and ligation-ready intermediates.
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