2,4-Dimethy-DL-Phenylalanine is a non-natural phenylalanine derivative in which the aromatic side chain bears two methyl substituents at the 2- and 4-positions, maintaining the amino acid backbone with an amino group and a carboxyl group. The molecule is provided as a DL mixture, so it contains both stereochemical configurations at the α-carbon, and the substituted benzyl side chain functions as a hydrophobic, sterically modified aromatic group relevant to structure-property studies and peptide analog design. In synthetic and chemical biology workflows, this amino acid is used as a building block for preparing modified peptides and for probing how aromatic substitution patterns affect conformation, binding, and labeling strategies that rely on altered side-chain chemistry.
CAT No: CP13903
2,4-Dimethy-DL-Phenylalanine is a DL-configured, non-natural phenylalanine analog featuring two methyl substituents at the 2- and 4-positions of the aromatic ring. This ring substitution pattern makes it a useful stereochemically defined amino acid building block for medicinal chemistry and peptidomimetic design where aromatic sterics and hydrophobicity are tuned without changing the amino acid backbone. In research settings, it is typically handled as a racemate and used to probe structure-property relationships in synthetic peptides and peptide-like scaffolds.
1. Peptidomimetic Building Blocks
2,4-Dimethy-DL-Phenylalanine is used by medicinal chemistry and chemical biology teams to introduce a substituted aromatic side chain into peptides, peptidomimetics, and constrained analog series. The 2,4-dimethyl substitution increases steric bulk around the phenyl ring and modulates hydrophobic character, which is valuable when optimizing binding-site complementarity in structure-activity relationship (SAR) studies. Because the material is supplied as a DL mixture, it is commonly selected for early-stage analog screening where racemic incorporation supports rapid generation of structure variants prior to any later chiral refinement.
2. SAR and Structure-Property Studies
2,4-Dimethy-DL-Phenylalanine supports SAR workflows aimed at quantifying how aromatic substitution patterns influence physicochemical behavior and downstream performance metrics of peptide-like molecules. Researchers use it to compare analogs bearing different ring substitution motifs while keeping the amino acid backbone constant, enabling clearer interpretation of how steric and electronic changes at the aromatic side chain affect synthetic scaffold behavior. This makes the compound particularly relevant for library synthesis and comparative studies in lead optimization campaigns, where substituted phenylalanine analogs are incorporated as standardized building blocks.
3. Peptide Analog Synthesis
2,4-Dimethy-DL-Phenylalanine is employed in custom peptide synthesis and analog manufacturing to construct peptide fragments and peptide-like intermediates containing a substituted aromatic residue. Synthetic chemists incorporate this amino acid to generate defined sequences used in assay development, protein-ligand interaction studies, and reference material preparation for analytical characterization of peptide analogs. The racemic nature is often leveraged when the goal is to obtain sufficient material for downstream evaluation of sequence-dependent properties across a series, rather than to isolate a single stereoisomer at the outset.
4. Pharmaceutical Intermediate Development
2,4-Dimethy-DL-Phenylalanine is also used as a specialty amino acid intermediate for downstream synthesis of substituted aromatic amino acid derivatives and peptide-derived intermediates used in medicinal chemistry programs. Process and development chemists rely on such building blocks to assemble non-natural residue motifs that are not readily accessible from standard proteinogenic amino acids. In this context, the compound functions as a practical input for generating diversified chemical matter, including protected forms and derivative scaffolds that can be further elaborated into advanced intermediates for research-scale lead optimization.
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