HYDROXYLAMINE WANG RESIN

Hydroxylamine Wang Resin

Hydroxylamine Wang Resin

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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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