4-Methoxy-D-Phenylalanine is a non-natural, aromatic amino acid derivative featuring a benzyl side chain bearing a methoxy substituent and a D-configured stereocenter at the alpha position. The molecule contains a free amino group and a free carboxyl group alongside an ether-functional methoxy substituent, enabling it to participate in standard amino acid coupling chemistry while providing a distinct electronic and steric profile relative to unsubstituted phenylalanine. In peptide and structure-activity study workflows, it is used as a defined stereochemical building block to introduce the methoxy-substituted phenyl side chain into synthetic peptides or related amino acid derivatives for probing binding interactions, conformational effects, and labeling or conjugation strategies.
CAT No: CP15502
4-Methoxy-D-Phenylalanine is a D-configured phenylalanine analog featuring a para-methoxy substituent on the aromatic ring, making it a non-proteinogenic amino acid building block for stereochemically defined peptide and peptidomimetic design. Its aromatic side chain supports hydrophobic and electronically tuned interactions, while the D-stereochemistry enables incorporation into sequences where resistance to proteolysis and conformational effects are often explored in chemical biology and medicinal chemistry workflows. Researchers commonly use this compound as a defined chiral intermediate to introduce a methoxy-substituted phenylalanine motif into synthetic peptides and SAR studies.
1. Peptidomimetic Building Block
4-Methoxy-D-Phenylalanine is used by peptide chemistry groups to construct peptidomimetics and modified peptide analogs where a D-amino acid residue is desired for stereochemical control. The para-methoxy group on the aromatic ring provides an additional handle for tuning aromatic electronics and polarity, which is frequently leveraged in structure-activity relationship (SAR) campaigns for receptor-binding ligands and enzyme-modulating peptide scaffolds. In these workflows, the compound functions as a discrete, well-defined chiral amino acid unit that can be incorporated into custom peptide synthesis to generate libraries of analogs with consistent side-chain identity.
2. Medicinal Chemistry SAR Studies
4-Methoxy-D-Phenylalanine supports medicinal chemistry optimization by enabling systematic variation of aromatic side-chain substitution patterns while maintaining a defined stereochemical configuration. Medicinal chemistry and chemical biology teams use this residue to probe how para-methoxy substitution influences binding mode, local conformational preferences, and overall physicochemical properties of peptide-like candidates. Because it is a non-natural amino acid, it is commonly selected to diversify chemical space beyond proteinogenic residues during lead refinement, particularly in studies where D-amino acid incorporation is used as a design element rather than a biological substrate.
3. Protein Engineering Analog Design
4-Methoxy-D-Phenylalanine is applied in protein and enzyme research programs that develop non-natural amino acid-containing analogs for mechanistic studies and protein engineering toolkits. Researchers use D-amino acid motifs to create chemically defined variants that can be compared against reference constructs, helping assess how stereochemistry and aromatic substitution affect structure, stability trends, or interaction patterns in engineered protein systems. In practice, this compound is typically employed as a synthetic building block for preparing peptide segments, binder scaffolds, or protein analogs where a methoxy-substituted phenylalanine residue is introduced to test specific design hypotheses.
4. Chiral Intermediate for Derivative Synthesis
4-Methoxy-D-Phenylalanine is also used by synthetic chemistry and pharmaceutical intermediate developers as a chiral starting material for preparing downstream amino acid derivatives and substituted aromatic building blocks. Its D-configuration and para-methoxy phenyl motif make it a useful precursor when teams need a consistent stereochemical element and a defined aromatic substitution pattern for further derivatization. This application is particularly relevant in process development and specialty chemical manufacturing contexts where controlled chiral identity is required to produce structurally consistent intermediates for research-grade peptide candidates and related chemical matter.
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