3-(4-Methyl-benzylsulfanyl)-propionic acid is a sulfur-containing, non-proteinogenic amino acid derivative featuring a propionic acid backbone bearing an amino group and a thioether side chain connected to a 4-methylbenzyl sulfanyl substituent. The molecule contains both amino and carboxyl functional groups and presents a thioether (S-alkyl) linkage that can influence polarity, hydrogen-bonding patterns, and chemical reactivity relative to canonical amino acid side chains. As a structurally modified amino acid building block, it is used in peptide and amino acid derivative synthesis and in structure-activity or chemical biology studies where a stable thioether side chain provides a defined handle for conjugation chemistry or for tuning physicochemical properties in labeled or functionalized peptide analogues.
CAT No: CP27479
CAS No:78981-22-3
Synonyms/Alias:Mpr(Mbzl)-OH;Mpa(Mbzl)-OH;S-(4-Methylbenzyl)-deamino-cysteine
3-(4-Methyl-benzylsulfanyl)-propionic acid is a thioether-functionalized amino-acid-like building block featuring a propionic acid backbone and a benzyl sulfanyl side chain. Its sulfur-containing substituent makes it a useful intermediate for constructing thioether motifs in medicinal chemistry and for preparing sulfur-bearing analogs used in structure-property studies. In synthetic and materials workflows, the free carboxylic acid provides a reliable handle for coupling chemistry, while the thioether side chain supports downstream derivatization to access thioether-containing scaffolds.
1. Thioether-Containing Intermediate Synthesis
3-(4-Methyl-benzylsulfanyl)-propionic acid is used by medicinal chemistry and specialty synthesis groups to build thioether-containing fragments for small-molecule libraries and analog series. The propionic acid functionality supports standard carboxylic acid activation and subsequent coupling steps, enabling incorporation into larger scaffolds while retaining the benzyl sulfanyl motif. This makes the compound a practical intermediate when a stable thioether (rather than a labile thiol) is required to probe chemical space, refine physicochemical properties, or support late-stage diversification.
2. Peptidomimetic And Amide Coupling
3-(4-Methyl-benzylsulfanyl)-propionic acid serves as a building block for preparing peptidomimetic structures and amide-containing analogs where a sulfur-bearing side chain is positioned along a short aliphatic spacer. Research teams developing constrained or non-natural amino-acid-like motifs often rely on carboxylic acid substrates like this to generate amide linkages with amines and to assemble modular structures for SAR (structure-activity relationship) evaluation. The thioether side chain provides a chemically stable sulfur functionality that can be carried through synthesis to the final analog stage.
3. Sulfur-Functionalized Scaffold Diversification
3-(4-Methyl-benzylsulfanyl)-propionic acid is applied in chemical biology and drug discovery support chemistry to diversify sulfur-containing scaffolds used for target-binding studies and chemical probe development workflows. The benzyl sulfanyl group offers a distinct electronic and steric contribution that can be leveraged when designing analogs to compare against oxygen- or hydrocarbon-substituted counterparts. Because the molecule retains a free carboxylic acid, it integrates readily into downstream derivatization strategies that require a single, well-defined anchoring functional group for attachment to larger frameworks.
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