2-Methoxy-DL-Phenylalanine is a methoxy-substituted phenylalanine derivative classified as an aromatic, non-proteinogenic amino acid with a benzyl side chain bearing a 2-methoxy substituent and a free amino group and carboxyl group. The "DL" designation indicates a racemic mixture of stereoisomers at the alpha carbon, and the molecule presents the typical amino acid zwitterionic functionality that can be used in coupling chemistry while the methoxy group modulates side-chain polarity and aromatic electronic character. As a substituted phenylalanine analogue, it is used in peptide synthesis and structure-activity or structure-property studies where incorporation of an aromatic residue with a methoxy-bearing side chain is required for conformational tuning, labeling strategies, or comparative analysis against unmodified phenylalanine.
CAT No: CP15303
2-Methoxy-DL-Phenylalanine is a methoxy-substituted phenylalanine analog supplied as a DL mixture, combining the amino acid backbone with a side-chain methoxy group that changes sterics and electronics relative to phenylalanine. This non-proteinogenic amino acid building block is commonly used in peptide and peptidomimetic synthesis to probe structure-property relationships and to introduce a methoxy-bearing aromatic residue into defined sequences. Its stereochemical DL composition supports screening workflows where racemic incorporation is acceptable for downstream evaluation, including medicinal chemistry lead optimization and analytical method development.
1. Peptidomimetic Building Blocks
2-Methoxy-DL-Phenylalanine is used by peptide chemists and medicinal chemistry groups to incorporate a methoxy-functionalized aromatic side chain into peptidomimetics and non-natural peptide libraries. The methoxy substituent provides a convenient handle for tuning polarity and hydrogen-bonding patterns within a sequence, which is useful when exploring how aromatic electronics and steric bulk influence conformation, binding-site interactions, or overall structure in SAR studies. Because the material is supplied as a DL mixture, it is frequently selected for parallel library synthesis and early-stage screening where racemic residue incorporation supports comparative evaluation across analog series.
2. Structure-Activity Relationship Studies
2-Methoxy-DL-Phenylalanine supports SAR and analog design efforts in chemical biology and drug discovery research by enabling systematic variation of aromatic side-chain substitution patterns. Researchers use this building block to replace phenylalanine-like residues with a methoxy-bearing variant, allowing direct comparison of how side-chain functionalization affects physicochemical behavior and molecular recognition trends in assay readouts. The amino acid format makes it practical for sequence-defined synthesis, while the DL stereochemistry is often leveraged in exploratory studies that prioritize side-chain effects over stereochemical purity during initial structure-function mapping.
3. Pharmaceutical Intermediate Development
2-Methoxy-DL-Phenylalanine is also employed in the development of pharmaceutical intermediates and specialty chemical syntheses where an amino acid-derived aromatic motif is required as a defined starting material. Process and R&D teams use it to access methoxy-substituted aromatic frameworks that can be carried forward into downstream transformations toward protected amino acid derivatives, coupling partners, or other intermediate classes relevant to medicinal chemistry programs. The stable, isolable amino acid scaffold helps standardize input material for batch-to-batch consistency in intermediate manufacturing workflows, particularly during lead optimization stages that demand reproducible chemical building blocks.
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