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

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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