HMBA-AM Resin: Acid-Base Labile Resin for Advanced Peptide and Organic Synthesis
HMBA-AM Resin (4-Hydroxymethylbenzoic acid amide resin) is a polystyrene-based resin functionalized with the HMBA linker (4-hydroxymethylbenzoic acid) attached via an amide bond to an aminomethylated (AM) support. This resin is designed for Fmoc-based solid-phase synthesis, where selective cleavage under mildly basic or acidic conditions is required to release C-terminal carboxamide peptides or intermediates with a free carboxyl group.
This resin is commonly used in fragment condensation, solid-phase organic synthesis (SPOS), and combinatorial chemistry, where orthogonal cleavage strategies are needed.
Specifications
Matrix: Polystyrene cross-linked with ~1% DVB
Linker: HMBA (4-hydroxymethylbenzoic acid)
Base Resin: Aminomethylated polystyrene
Functional Group: HMBA – amide bound to resin
Loading: Typically 0.4–1.0 mmol/g
Particle Size: 100–200 mesh (approx. 75–150 µm)
Cleavage Conditions: Mild base (e.g., hydrazine) or acid (e.g., dilute TFA or HFIP)
C-Terminal Product: Carboxamide (-CONH₂) or carboxylic acid (-COOH), depending on conditions
Key Features
Dual Cleavage Options: Cleavable under mild acid or base, enabling orthogonal deprotection strategies
Carboxamide-terminating peptides: Produces biologically relevant amide termini
Versatile linker: Suitable for both peptide and non-peptide synthesis
Compatible with Fmoc SPPS: Fully integrates into standard protocols
Stable under synthesis conditions: Withstands base, acid, and coupling reagents
Applications
Peptide synthesis with C-terminal amides or free acids
Fragment-based synthesis and segment ligation strategies
Solid-phase organic synthesis (SPOS)
Combinatorial library generation with orthogonal cleavage options
Development of amide-containing bioactive molecules
Cleavage Conditions
| Condition | Result | Reagents |
|---|---|---|
| Mild acid (e.g., 1% TFA or HFIP) | Free carboxylic acid | HFIP/DCM (1:4), 1–2 h |
| Hydrazine or base (e.g., hydrazinolysis) | Carboxamide | 2% hydrazine/DMF, 1–4 h |
| TFA (95%) | Complete cleavage | Used for global deprotection (when needed) |
Handling & Storage
Store dry, away from light and moisture
Pre-swell in DMF or DCM before use
Handle using standard SPPS protocols
Stable for long-term storage under inert conditions
Conclusion
HMBA-AM Resin offers synthetic chemists a flexible, orthogonally cleavable resin ideal for crafting amide-terminated peptides or building carboxylic acid intermediates in SPPS and organic synthesis workflows. Its ability to respond to both mild acidic and basic conditions makes it an excellent choice for multi-step, strategic synthesis protocols.
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