3,5-Dimethy-D-Phenylalanine is a non-proteinogenic, D-configured phenylalanine analogue featuring a benzyl side chain bearing two additional methyl substituents at the 3 and 5 positions of the aromatic ring. The molecule contains both an amino group and a carboxyl group characteristic of amino acids, while the D stereochemistry is retained at the alpha carbon and the substituted phenyl ring provides a more hydrophobic, sterically modified aromatic surface compared with unsubstituted phenylalanine. As a structurally modified amino acid, it is used in peptide synthesis and structure-activity or structure-property studies to introduce an altered aromatic environment, and it can also serve as a defined building block for chemical labeling or analytical method development where a methyl-substituted phenylalanine motif is required.
CAT No: CP14302
3,5-Dimethy-D-Phenylalanine is a D-configured, non-proteinogenic amino acid featuring a sterically demanding, hydrophobic dimethyl-substituted phenyl side chain. This structural motif is frequently leveraged in peptide drug discovery and peptidomimetic design to tune backbone/side-chain shape and local physicochemical properties. As a chiral amino acid building block, it is typically used where stereochemical control and non-natural side-chain substitution are required to probe structure-activity relationships and improve chemical stability profiles in synthetic peptide-like systems.
1. Peptidomimetic Building Blocks
3,5-Dimethy-D-Phenylalanine is used as a non-natural amino acid building block for constructing peptidomimetics and peptide-like scaffolds in medicinal chemistry programs. Researchers incorporate this D-amino acid into short peptides, constrained analogs, or SAR libraries to introduce a bulky, hydrophobic side chain that can influence conformational preferences and interaction patterns with biological targets. Its defined stereochemistry supports systematic comparison across analog series, particularly when D-configuration and 3,5-dimethyl substitution are used as design variables rather than relying on proteinogenic residues.
2. Peptide Library SAR Development
3,5-Dimethy-D-Phenylalanine is commonly employed in peptide library synthesis workflows where site-specific substitution is needed to map how side-chain sterics and hydrophobicity affect binding or functional readouts. Chemical biology and medicinal chemistry groups use this residue during custom peptide synthesis to generate analog panels with controlled sequence placement, enabling structure-activity relationship studies across multiple positions. The dimethyl-substituted aromatic side chain provides a distinct steric/electronic environment compared with standard phenylalanine derivatives, making it a practical choice for differentiating analog behavior in parallel screening campaigns.
3. Pharmaceutical Intermediate Synthesis
3,5-Dimethy-D-Phenylalanine is also used as a chiral intermediate in the development of non-natural amino acid derivatives for downstream pharmaceutical intermediate manufacturing. Process development teams and specialty chemical manufacturers rely on well-defined stereochemical amino acid inputs to prepare higher-value intermediates used in larger synthetic sequences, including protected amino acid derivatives and coupling-ready formats for subsequent assembly steps. The aromatic dimethyl side chain is particularly relevant when the target intermediate requires a hydrophobic, sterically tuned fragment that is difficult to reproduce using simpler aromatic building blocks.
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