2,4-Dimethy-L-Phenylalanine is a naturally derived, proteinogenic amino acid analogue in which the phenyl side chain of L-phenylalanine is substituted with two methyl groups at the 2- and 4-positions, yielding a substituted aromatic, hydrophobic side chain. The molecule contains a free amino group and a free carboxyl group on the α-carbon, with the stereochemistry indicated as L, and its side chain bears a substituted benzyl aromatic functionality that can participate in hydrophobic and π-interactions while lacking additional strongly ionizable groups. In peptide chemistry and protein engineering workflows, this amino acid is used as a building block to introduce sterically and electronically modified aromatic residues for structure-activity studies, conformational probing, and the preparation of peptides or peptide mimetics with altered side-chain packing.
CAT No: CP13901
2,4-Dimethy-L-Phenylalanine is a stereochemically defined, non-proteinogenic amino acid featuring a L-configuration and a sterically enriched aromatic side chain with two methyl substituents at the 2- and 4-positions. This substituted phenylalanine motif is used as a structural building block to introduce increased hydrophobicity and conformational/steric modulation into peptides and peptide-derived scaffolds. In peptide chemistry and medicinal chemistry programs, it is valued for enabling SAR studies where aromatic ring substitution pattern and side-chain bulk are key variables.
1. Peptide SAR Building Blocks
2,4-Dimethy-L-Phenylalanine is used by peptide medicinal chemistry groups to construct peptide analogs for structure-activity relationship (SAR) evaluation, where aromatic substitution and steric profile are tuned systematically. Incorporating this amino acid into short peptides or peptidomimetic sequences helps researchers probe how ring methylation at defined positions influences local packing, hydrophobic surface area, and side-chain orientation. The L-stereocenter supports consistent backbone geometry during assembly, while the 2,4-dimethyl substituted phenyl group provides a distinct physicochemical signature compared with unsubstituted phenylalanine, enabling clearer interpretation of structure-property trends.
2. Protein Engineering Probes
2,4-Dimethy-L-Phenylalanine is applied in protein engineering and chemical biology workflows that require site-specific incorporation of non-canonical aromatic residues to perturb local structure and side-chain environment. Researchers use such substituted amino acids to create protein variants or peptide segments that report on how steric bulk and aromatic electronics affect folding, stability, or interaction interfaces in model systems. The defined L-configuration and rigid aromatic side chain make it a practical choice for designing constructs where subtle changes in aromatic substitution pattern are expected to alter packing or binding-site microenvironments, supporting mechanistic studies in biophysical and structural biology settings.
3. Peptidomimetic Medicinal Chemistry
2,4-Dimethy-L-Phenylalanine is commonly used in medicinal chemistry to prepare peptidomimetic intermediates and analog libraries that explore aromatic ring substitution as a lever for optimizing lead series. Teams developing constrained or lipophilicity-tuned peptide-like scaffolds often select substituted phenylalanine derivatives to modulate hydrophobic character and steric complementarity at binding interfaces. Because the side chain is a substituted phenyl ring rather than a flexible aliphatic group, the residue provides a reproducible handle for medicinal chemists to vary aromatic topology while maintaining a consistent amino-acid backbone framework for downstream derivatization and analog synthesis.
4. Analytical Reference Standards
2,4-Dimethy-L-Phenylalanine is used as an analytical reference material in workflows that quantify or verify the presence of substituted aromatic residues in custom peptides, peptide hydrolysates, and related synthetic intermediates. Analytical chemists and quality-focused research groups employ it to support method development for LC-based assays and mass spectrometry characterization where an exact, structurally defined amino acid standard improves identification confidence and calibration. The distinct 2,4-dimethyl substitution pattern helps differentiate it from common phenylalanine species, making it useful when confirming incorporation fidelity in peptide synthesis and when screening peptide fractions for the targeted residue composition.
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