2,6-Dimethy-D-Phenylalanine is a non-proteinogenic, stereochemically specified amino acid derivative featuring a phenylalanine backbone with two methyl substituents at the 2 and 6 positions of the aromatic ring and a D-configuration at the α-carbon. The molecule contains a free amino group and a free carboxyl group, while the sterically hindered, ortho-disubstituted phenyl side chain provides a bulky hydrophobic aromatic functionality that can influence conformational preferences and side-chain interactions in peptide contexts. As a modified amino acid building block, it is used in peptide synthesis and structure-activity or structure-property studies where altered aromatic substitution patterns and D-amino acid stereochemistry are used to probe effects on peptide folding, stability, and binding.
CAT No: CP14102
2,6-Dimethy-D-Phenylalanine is a D-configured, non-proteinogenic amino acid featuring a sterically demanding 2,6-dimethyl-substituted phenyl side chain. This increased bulk and altered aromatic substitution pattern make it a useful building block for designing peptidomimetics and modified peptides where side-chain shape and hydrophobic character are tuned. Researchers commonly use this amino acid to introduce conformational and steric effects at specific positions during synthetic peptide construction.
1. Peptidomimetic Building Block
2,6-Dimethy-D-Phenylalanine is used by medicinal chemistry and chemical biology groups to prepare peptidomimetic scaffolds and positionally defined modified peptides. The D-configuration and the 2,6-dimethyl aromatic substitution provide a practical way to modulate steric environment and hydrophobic surface presentation relative to standard phenylalanine analogs. In downstream workflows, this amino acid is typically incorporated into peptide-like structures to generate defined analog series for structure-activity relationship studies and to probe how side-chain bulk influences folding, presentation, and interaction patterns in synthetic systems.
2. Protease Resistance Probes
2,6-Dimethy-D-Phenylalanine is frequently selected for developing protease-stability and degradation-pattern studies in peptide research. By installing a D-amino acid residue with a sterically hindered, 2,6-dimethyl-substituted phenyl side chain, researchers can create peptide analogs that differ in local steric shielding and backbone stereochemical presentation. Such constructs are commonly used in laboratory workflows that compare degradation behavior across analog panels, supporting chemical biology investigations into how specific residue identity and steric demand affect enzymatic processing of peptide substrates.
3. Structure-Activity Analogue Synthesis
2,6-Dimethy-D-Phenylalanine supports analog generation for SAR campaigns where aromatic substitution and stereochemistry are treated as design variables. Synthetic chemists incorporate this residue into short peptide fragments and constrained peptide-like motifs to systematically vary side-chain sterics while keeping other structural elements constant. The resulting analogs are then used in screening or characterization pipelines to map structure-property relationships, including how changes in aromatic bulk and D-stereochemistry translate into differences in physicochemical behavior and interaction tendencies relevant to chemical biology assays.
4. Chiral Amino Acid Intermediate Use
2,6-Dimethy-D-Phenylalanine is also used as a chiral amino acid building block in manufacturing and R&D settings that require a defined D-stereocenter and a substituted aromatic side chain. Teams developing specialty intermediates leverage its fixed stereochemistry to reduce variability in downstream derivative synthesis, including the preparation of further amino acid derivatives for custom peptide synthesis. This usage is especially common when the 2,6-dimethyl phenyl motif must be retained as a steric element throughout multi-step assembly of peptide-like materials and research-grade chemical libraries.
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