3,5-Dimethy-DL-Phenylalanine is a substituted phenylalanine derivative featuring a benzyl side chain bearing two methyl substituents at the 3 and 5 positions, classifying it as a non-natural, aryl-substituted amino acid. The molecule contains a free amino group and a free carboxyl group on the alpha carbon and is provided as a DL mixture, reflecting an unspecified stereochemical composition between the enantiomeric forms. Its sterically and electronically modified aromatic side chain makes it a structural analog for peptide and structure-activity studies, where incorporation of the substituted phenylalanine residue can be used to probe effects of aromatic substitution on peptide conformation, binding interfaces, or analytical retention behavior.
CAT No: CP14303
3,5-Dimethy-DL-Phenylalanine is a DL (racemic) phenylalanine analog bearing two methyl substituents at the 3 and 5 positions of the aromatic ring. This non-proteinogenic amino acid building block is used in peptide and peptidomimetic design where side-chain sterics and hydrophobic/aromatic character are tuned without changing the amino acid backbone framework. Its racemate form supports exploratory structure-property studies and intermediate development when stereochemical resolution is not yet required.
1. Peptidomimetic Building Blocks
3,5-Dimethy-DL-Phenylalanine is commonly incorporated into peptide-like scaffolds and peptidomimetics during lead optimization to probe how increased aromatic substitution affects conformation, local packing, and physicochemical behavior. Medicinal chemistry and chemical biology teams use this amino acid to generate analog series for structure-activity relationship (SAR) work, especially when the goal is to modulate hydrophobicity and steric bulk around the phenyl side chain. The DL stereochemistry is often selected for early-stage library synthesis and rapid analog generation, with downstream stereochemical refinement handled separately if needed.
2. SAR And Conformational Studies
3,5-Dimethy-DL-Phenylalanine is used to create controlled analog sets for studying how ring substitution patterns influence peptide backbone presentation and side-chain interactions in solution and in binding assays. Researchers in medicinal chemistry and protein/peptide engineering workflows employ this analog to vary aromatic substitution while keeping the amino acid backbone constant, enabling more interpretable comparisons across series. In practice, the racemic mixture supports efficient screening of substitution effects before committing to enantiopure materials for detailed conformational or stereochemically resolved studies.
3. Pharmaceutical Intermediate Development
3,5-Dimethy-DL-Phenylalanine serves as a practical chiral-amino-acid-derived intermediate for downstream synthesis of substituted aromatic amino acid derivatives used in medicinal chemistry programs. Process and development chemists leverage its defined substituted phenylalanine motif to access analogs that require the 3,5-dimethyl aromatic pattern as a structural feature, including further functionalization on the amino acid side chain or conversion into protected forms compatible with peptide coupling strategies. The DL format is frequently used during route scouting and intermediate library preparation, where stereochemical resolution can be deferred until a specific stereochemical outcome is prioritized.
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