2,6-Dimethy-DL-Phenylalanine is a non-natural, phenylalanine-derived amino acid featuring a benzyl side chain bearing two methyl substituents at the 2 and 6 positions, classifying it as a sterically modified aromatic amino acid. The molecule contains a free amino group and a free carboxyl group on the α-carbon and is supplied as a DL mixture, producing both stereochemical forms at the chiral center while retaining the substituted aromatic functionality that can modulate hydrophobicity and steric effects in peptide environments. In peptide synthesis and structure-activity studies, this sterically hindered aromatic residue is used to introduce bulky, methyl-substituted phenylalanine analogues for examining conformational preferences, side-chain packing, and effects on chemical labeling or analytical characterization of amino acid-containing constructs.
CAT No: CP14103
CAS No:132466-22-9
Synonyms/Alias:2-amino-3-(2,6-dimethylphenyl)propanoicacid;132466-22-9;2,6-Dimethy-DL-Phenylalanine;103854-26-8;NSC21952;AC1L5GIF;SCHEMBL2703289;2,6-Dimethyl-DL-Phenylalanine;CTK8C0060;H-DL-Phe(2,6-Me2)-OH;MolPort-021-942-989;5976AA;ANW-63995;NSC-21952;AKOS006277199;AM83302;AK-57857;AM002120;KB-18385;SC-69513;TC-152740;FT-0697555;I14-37213;3B3-075773
2,6-Dimethy-DL-Phenylalanine is a non-proteinogenic, DL-configuration phenylalanine analog bearing two methyl substituents at the 2- and 6-positions of the aromatic ring. This sterically hindered, hydrophobic side chain is frequently used as a structural probe and as a building block in peptide and peptidomimetic design where aromatic shielding or altered conformational preferences are desired. Because it is supplied as a racemic mixture, it is commonly selected for synthesis and screening workflows that prioritize chemical reactivity and side-chain effects over stereodefined incorporation.
1. Peptidomimetic Building Block
2,6-Dimethy-DL-Phenylalanine is used in peptide synthesis and peptidomimetic development to introduce a sterically encumbered, dimethyl-substituted phenylalanine residue into bioactive peptide analogs and SAR libraries. Medicinal chemistry groups frequently incorporate this scaffold to probe how aromatic ring substitution patterns influence local structure, backbone-side-chain packing, and overall hydrophobic character in sequence-defined constructs. The racemic (DL) form is particularly practical for early-stage library generation, where multiple analogs are compared side-by-side and stereochemical resolution is handled later if needed.
2. Structure-Activity Relationship Studies
2,6-Dimethy-DL-Phenylalanine supports structure-activity relationship work in chemical biology and drug discovery research by enabling systematic variation of aromatic side-chain sterics and electronics across a series of analogs. Researchers use this residue to evaluate how ortho-dimethyl substitution modulates molecular recognition motifs, including changes in steric accessibility around the aromatic ring and altered interactions with binding pockets in receptor or enzyme assays. In these workflows, the compound is valued as a defined amino acid building block that can be incorporated into short peptides, constrained peptidomimetics, or assay-ready intermediates for parallel testing.
3. Chemical Biology Probes
2,6-Dimethy-DL-Phenylalanine is applied as a chemical biology probe component when aromatic shielding effects are used as a design element to study structure-dependent behavior in protein-peptide interactions. By installing an ortho-dimethyl substituted phenylalanine residue, researchers can create peptide probes with reduced exposure of the aromatic face, which helps differentiate contributions from steric accessibility versus backbone composition in binding and recognition studies. This makes the material useful for generating sequence-defined probe panels used in interaction mapping, competition experiments, and mechanistic characterization of peptide recognition features.
4. Pharmaceutical Intermediate Development
2,6-Dimethy-DL-Phenylalanine is also used as a pharmaceutical intermediate building block for downstream synthesis of substituted amino acid derivatives and peptide fragments employed in medicinal chemistry programs. Industrial and contract synthesis teams rely on well-defined amino acid analogs like this to prepare customized intermediates for assembling larger molecules, including protected amino acid derivatives used in fragment coupling and stepwise construction of peptide-like scaffolds. The dimethylated aromatic side chain provides a robust handle for introducing sterically modified aryl motifs into final candidates while maintaining a standardized amino acid starting material for scalable synthesis planning.
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