2,4-Dimethy-D-Phenylalanine is a non-proteinogenic, D-configured phenylalanine derivative bearing two methyl substituents at the 2- and 4-positions of the aromatic ring, which modifies the side-chain sterics and hydrophobic character relative to unmodified phenylalanine. The molecule contains a free amino group and a free carboxyl group on the α-carbon, while the substituted benzyl side chain provides a substituted phenyl functionality that can participate in hydrophobic and aromatic interactions during peptide assembly. It is used in peptide synthesis and structure-activity or chemical biology studies where altered aromatic substitution patterns and D-amino acid stereochemistry are employed to probe conformational effects, binding preferences, and stability in peptide-like materials.
CAT No: CP13902
2,4-Dimethy-D-Phenylalanine is a D-configuration, non-proteinogenic phenylalanine analog bearing two methyl substituents at the 2- and 4-positions of the aromatic ring. This sterically and electronically modified side chain is commonly used in peptidomimetic and medicinal chemistry programs to probe how aromatic substitution patterns influence conformation, stability, and structure-activity relationships. As a chiral amino acid building block, it is typically handled as a synthetic intermediate for incorporation into peptides and peptide-like scaffolds where backbone stereochemistry and side-chain bulk are key design variables.
1. Peptidomimetic Building Blocks
2,4-Dimethy-D-Phenylalanine is used as a stereodefined amino acid building block for constructing peptidomimetics and modified peptide analogs in medicinal chemistry and chemical biology research. The D-configuration supports the design of non-natural peptide backbones aimed at controlling local stereochemistry, while the dimethyl-substituted phenyl ring provides increased steric bulk and altered aromatic electronics. Researchers incorporate this residue into solution-phase or solid-phase peptide synthesis workflows when they need a specific, non-proteinogenic aromatic side chain to tune folding propensity, conformational preferences, or SAR outcomes in lead optimization studies.
2. Structure-Activity Relationship Studies
2,4-Dimethy-D-Phenylalanine is frequently selected for SAR campaigns where aromatic ring substitution is treated as a tunable chemical handle. Medicinal chemistry groups use this residue to systematically vary side-chain sterics and hydrophobic/aromatic character within a peptide or peptidomimetic series, enabling direct comparison of analogs that differ only by the aromatic substitution pattern. Because the compound is a discrete, chiral amino acid building block, it supports reproducible analog synthesis and downstream characterization (e.g., LC-MS confirmation of peptide composition and purified scaffold profiling), helping teams attribute observed property changes to the introduced 2,4-dimethyl phenyl motif.
3. Protease-Resistant Analog Design
2,4-Dimethy-D-Phenylalanine is applied in the development of peptide-like inhibitors and protease-resistant analogs where non-natural stereochemistry and sterically demanding aromatic side chains are used to reduce susceptibility to enzymatic processing. Peptide engineering teams incorporate this D-amino acid residue into constrained or substituted peptide backbones to evaluate how aromatic substitution and D-configuration affect degradation trends in assay panels. In these workflows, the product functions as a targeted residue for generating matched analogs that differ at defined positions, supporting mechanistic interpretation of stability-related SAR without changing the overall scaffold architecture.
4. Chiral Intermediate For Synthesis
2,4-Dimethy-D-Phenylalanine serves as a chiral intermediate for downstream synthesis of specialized amino acid derivatives and peptide fragments used in research and specialty chemical manufacturing. Organic synthesis groups and process-development teams use it to access D-configured aromatic amino acid motifs that are difficult to obtain from simpler phenylalanine precursors without introducing the required 2,4-dimethyl substitution pattern. This makes the compound useful when building blocks must retain stereochemical integrity and the aromatic substitution pattern must be preserved through subsequent derivatization steps leading to peptide segments, analog libraries, or other non-natural amino acid-containing intermediates.
1. SERS spectrum of the peptide thymosin‐β4 obtained with Ag nanorod substrate
4. The spatiotemporal control of signalling and trafficking of the GLP-1R
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