3-(4-Hydroxy-phenyl)-propionic acid-OSu is an amino-acid derivative featuring a 3-(4-hydroxyphenyl)propionic acid scaffold linked to an N-hydroxysuccinimide (OSu) ester, classifying it as an activated carboxylic acid for amide-forming coupling. The molecule contains a phenolic hydroxyl on the aromatic ring and a carboxyl-derived OSu leaving group, with the reactive ester enabling chemoselective acyl transfer to nucleophiles such as primary amines while retaining the propionic acid carbon framework. In synthesis and chemical biology workflows, it is employed as an acylating reagent to prepare amide-linked conjugates for molecular labeling, bioconjugation, and the construction of amino-acid-derived linkers or building blocks for further peptide or protein modification.
CAT No: CP27028
CAS No:34071-95-9
Synonyms/Alias:Bolton-Hunterreagent;34071-95-9;Rudingerreagent;SHPP;1-{[3-(4-hydroxyphenyl)propanoyl]oxy}-2,5-pyrrolidinedione;Succinimido3-(4-hydroxyphenyl)propionate;Bolton-Hunterreagentprecursor;3-(4-Hydroxyphenyl)propionicacidN-hydroxysuccinimideester;3-(p-Hydroxyphenyl)propionicacid-N-hydroxysuccinimideester;35268-49-6;N-[(4-Hydroxyhydrocinnamoyl)oxy]succinimide;N-Succinimidyl3-(4-hydroxyphenyl)propionate;RudingerEO(1/4)A;AC1Q6LL4;H1256_ALDRICH;H1256_SIGMA;SCHEMBL112099;AC1L40Z9;AC1Q78U8;Jsp006197;56189_FLUKA;56189_SIGMA;CTK8D6688;MolPort-006-149-382;ZINC395677
3-(4-Hydroxy-phenyl)-propionic acid-OSu is an N-hydroxysuccinimide (OSu) activated ester of 3-(4-hydroxyphenyl)propionic acid, designed for coupling to primary amine nucleophiles under mild, aqueous-compatible conditions. The presence of the phenolic side chain provides an additional functional handle for downstream conjugation, surface chemistry, or analytical readouts, while the OSu leaving group supports efficient amide-bond formation in bioconjugation workflows. This reagent format is commonly selected when researchers need a controlled, high-reactivity acylating agent for attaching the 3-(4-hydroxyphenyl)propionyl motif to proteins, peptides, or other amine-containing biomolecules.
1. Amine Bioconjugation
3-(4-Hydroxy-phenyl)-propionic acid-OSu is used to introduce the 3-(4-hydroxyphenyl)propionyl group onto lysine residues and N-termini of proteins and peptides via amide-bond formation. Bioconjugation teams in chemical biology and biomaterials development rely on OSu-activated esters to achieve practical coupling efficiency while maintaining compatibility with aqueous buffers and typical biomolecule handling. The retained phenolic functionality in the resulting conjugate is useful when the labeling needs an additional chemical handle for subsequent derivatization, immobilization, or orthogonal functionalization steps.
2. Protein Labeling For Assays
3-(4-Hydroxy-phenyl)-propionic acid-OSu supports preparation of labeled protein reagents used in binding studies, enzyme-interaction experiments, and analytical assay development where a defined aromatic moiety is advantageous for detection or secondary chemistry. Researchers often choose this OSu ester format to rapidly install the acyl group onto amine-bearing targets, enabling consistent conjugate construction for method development and comparative studies. The phenolic group in the conjugate can also be leveraged to tune reactivity in downstream steps, such as affinity tag construction or secondary labeling strategies.
3. Surface Immobilization Chemistry
3-(4-Hydroxy-phenyl)-propionic acid-OSu is applied in workflows that functionalize amine-containing surfaces or polymers with a phenolic aromatic linker motif. Materials scientists and industrial R&D teams use OSu-activated esters to covalently attach acyl groups to substrates bearing primary amines, including amine-functional resins, coatings, and polymeric supports used in biosensor and affinity-material development. After immobilization, the phenolic functionality in the surface-bound layer provides a chemically meaningful group for further modification, stability-oriented surface tuning, or integration into multi-step material assembly.
4. Peptide Conjugate Building
3-(4-Hydroxy-phenyl)-propionic acid-OSu is commonly used to generate peptide conjugates where the goal is to acylate peptide N-termini or lysine side-chain amines with the 3-(4-hydroxyphenyl)propionic acid motif. Peptide chemistry groups use this activated ester to streamline the preparation of modified peptide standards and conjugates for chemical biology experiments, including structure-function studies that require a specific aromatic appendage. The OSu activation enables efficient coupling to amine handles on peptides without requiring pre-activation of the acid, and the phenolic group in the resulting peptide conjugate supports subsequent derivatization or analytical characterization.
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