3,4-Dimethy-DL-Phenylalanine is a substituted phenylalanine derivative in which the phenyl side chain bears two methyl substituents at the 3,4-positions, making it a non-standard amino acid analog used in peptide and structure-activity studies. The molecule contains both an amino group and a carboxyl group characteristic of amino acid building blocks, with the "DL" designation indicating a racemic mixture of stereoisomers at the α-carbon. As a chemically modified aromatic amino acid, it can be employed as a substrate-like component in peptide synthesis workflows and as a labeled or substituent-variant reagent for probing how side-chain steric and electronic changes influence peptide conformation and binding in chemical biology experiments.
CAT No: CP14203
3,4-Dimethy-DL-Phenylalanine is a DL (racemic) phenylalanine analog bearing two methyl substituents at the 3,4-positions of the aromatic ring. This non-proteinogenic, sterically modified aromatic side chain makes it a practical building block for preparing substituted amino acid motifs used in peptide and peptidomimetic structure-activity relationship studies. Researchers also use this compound as a chiral-synthesis starting material to access defined stereochemical variants when downstream enantiopure material is required for SAR, conformational studies, or medicinal chemistry lead optimization.
1. Peptidomimetic SAR Building Blocks
3,4-Dimethy-DL-Phenylalanine is used to introduce a sterically enriched, methyl-substituted phenylalanine side chain into peptide-like scaffolds for medicinal chemistry and peptidomimetic development. In practice, medicinal chemistry groups incorporate this aromatic amino acid analog into custom peptide synthesis to probe how ring substitution affects physicochemical properties and structure-activity relationships, including changes in local sterics and aromatic packing within binding-site models. The DL stereochemical mixture is commonly selected for early-stage library synthesis where rapid analog generation is prioritized, with later resolution or stereochemical refinement performed as part of the optimization workflow.
2. Non-Proteinogenic Peptide Synthesis
3,4-Dimethy-DL-Phenylalanine serves as a non-natural amino acid building block for assembling substituted peptides that incorporate modified aromatic residues beyond the standard proteinogenic set. Peptide synthesis teams use this analog to create sequence-defined constructs for chemical biology tool development, receptor/ligand binding studies, and mechanistic experiments where aromatic ring substitution is a controlled variable. The methyl substitution pattern on the phenyl ring provides a direct handle for comparing analog series against unsubstituted phenylalanine derivatives, while the racemic form supports parallel synthesis of stereochemical variants and downstream purification strategies.
3. Chiral Resolution Feedstock
3,4-Dimethy-DL-Phenylalanine is frequently handled as a starting feedstock for chiral synthesis workflows aimed at obtaining enantiopure substituted phenylalanine derivatives. In downstream development, process chemists and synthetic method developers may resolve the racemate or convert it into stereochemically defined intermediates to support structure-stereochemistry investigations in medicinal chemistry. This use is particularly relevant when the aromatic 3,4-dimethyl substitution is retained as a key structural feature while the stereochemical outcome becomes important for interpreting activity trends, optimizing selectivity, or improving reproducibility across analog series.
4. Pharmaceutical Intermediate Development
3,4-Dimethy-DL-Phenylalanine is also used as a specialty amino acid intermediate in the preparation of substituted aryl-containing fragments that feed into larger medicinal chemistry programs. Pharmaceutical intermediate development teams rely on this type of amino acid analog to build toward more complex heterocycles, constrained side-chain motifs, or protected building blocks used in subsequent coupling steps. The presence of the amino acid functionality and the substituted aromatic ring allows the compound to be positioned early in a synthetic route where the 3,4-dimethylphenyl motif must be carried through and ultimately incorporated into final candidate structures.
1. An Open-label, Single-center, Safety and Efficacy Study of Eyelash Polygrowth Factor Serum
5. SERS spectrum of the peptide thymosin‐β4 obtained with Ag nanorod substrate
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