3-(4-Methoxy-benzylsulfanyl)-3-methyl-butyric acid is a non-proteinogenic, sulfur-containing amino acid derivative featuring a branched aliphatic backbone bearing a carboxylic acid and a primary amino group, along with a 3-methyl substitution and a thioether substituent linked to a 4-methoxybenzyl group. The side chain contains a sulfanyl (thioether) linkage that provides a soft sulfur donor for thioether-based conjugation or coordination chemistry, while the aromatic ring bears a para-methoxy substituent that modulates polarity and electronic character; stereochemistry is not specified in the name. In synthetic and chemical biology contexts, this molecule is used as a precursor for preparing modified amino acid building blocks and peptides where a thioether-functional side chain is required for structure-activity studies, bioconjugation handle installation, or downstream derivatization to more reactive sulfur-containing functionalities.
CAT No: CP26922
CAS No:268219-99-4
Synonyms/Alias:3-(4-METHOXY-BENZYLSULFANYL)-3-METHYL-BUTYRICACID;268219-99-4;SCHEMBL8746111;CTK4F8566;ZINC2560758;5197AH;AKOS025404110;AK186609;OR250760;K-6884;S-(4-METHOXYBENZYL)-DEAMINO-PENICILLAMINE
3-(4-Methoxy-benzylsulfanyl)-3-methyl-butyric acid is a sulfur-containing, non-proteinogenic amino acid derivative featuring a thioether side chain and a branched, methyl-substituted backbone. Its carboxylic acid functionality makes it a practical building block for downstream synthesis of peptidomimetic and medicinal chemistry scaffolds where controlled hydrophobicity and thioether incorporation are required. The aromatic methoxybenzyl sulfanyl motif provides a stable sulfur handle that is routinely leveraged in structure-activity relationship (SAR) studies and intermediate diversification workflows.
1. Peptidomimetic Building Blocks
3-(4-Methoxy-benzylsulfanyl)-3-methyl-butyric acid is used by medicinal chemistry and peptide-mimetic research groups to construct side-chain-defined analogs that emulate amino acid substitution patterns while introducing a thioether-bearing aromatic group. In custom peptide and peptidomimetic assembly programs, the carboxylic acid serves as a reliable functional group for conversion into activated coupling partners or incorporation into larger fragments, enabling systematic variation of sterics and lipophilicity around a branched backbone. This derivative is particularly valued when the target scaffold design benefits from a stable thioether substituent rather than a more labile sulfur functionality.
2. Pharmaceutical Intermediate Diversification
3-(4-Methoxy-benzylsulfanyl)-3-methyl-butyric acid supports pharmaceutical intermediate development where a protected, side-chain-bearing amino acid derivative is needed for iterative synthesis. Process and synthesis teams commonly incorporate this compound as a defined sulfur-containing intermediate to access analog series with consistent stereochemical and connectivity features, facilitating parallel library synthesis for SAR and lead optimization. The methoxybenzyl sulfanyl group provides a chemically stable handle for further downstream transformations in medicinal chemistry routes, while the carboxylic acid enables straightforward progression to coupling-ready forms used in multi-step intermediate sequences.
3. Structure-Activity Relationship Studies
3-(4-Methoxy-benzylsulfanyl)-3-methyl-butyric acid is frequently selected for SAR studies that probe how thioether substitution and aromatic methoxybenzyl character influence potency-related properties in small-molecule and peptidomimetic candidates. Research groups use it to generate analogs that vary sulfur-containing side-chain volume and electronic character while keeping the backbone substitution pattern consistent through the branched 3-methyl motif. This makes the compound useful in iterative design cycles where chemists need a structurally specific, sulfur-bearing building block to map structure-property relationships across closely related series.
4. Chiral Intermediate Development
3-(4-Methoxy-benzylsulfanyl)-3-methyl-butyric acid is also applied in chiral synthesis workflows where amino acid-derived fragments are used to access enantiomerically defined intermediates for downstream stereochemical control. Synthetic chemistry teams can leverage the amino acid-like carboxylic acid functionality and the side-chain-defined thioether/aromatic motif to build stereochemically constrained intermediates for subsequent fragment coupling or scaffold elaboration. This use case is common in programs that require consistent stereochemical outcomes across a series of sulfur-containing analogs, including peptidomimetic and medicinal chemistry targets.
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