3-Methoxy-L-Phenylalanine is a natural amino acid derivative classified as an L-phenylalanine analogue, featuring a benzyl side chain bearing a methoxy substituent at the 3-position. The molecule contains both an amino group and a carboxyl group on the α-carbon framework characteristic of amino acids, with the side chain functioning as an aromatic ether that can influence polarity, hydrogen-bonding patterns, and hydrophobic interactions in peptide contexts. As a free (unprotected) amino acid, it is used in peptide synthesis and structure-activity or structure-property studies to introduce a defined aromatic methoxy functionality and to support chemical labeling or analytical investigations of methoxy-substituted phenylalanine residues.
CAT No: CP15401
CAS No:33879-32-2
Synonyms/Alias:33879-32-2;3-Methoxy-L-Phenylalanine;(S)-2-AMINO-3-(3-METHOXYPHENYL)PROPANOICACID;(S)-2-Amino-3-(3-methoxyphenyl)propionicacid;3-Methoxyphenylalanine;L-3-MEO-PHE-OH;(S)-2-Amino-3-(3-methoxy-phenyl)-propionicacid;H-PHE(3-OME)-OH;(2S)-2-AMINO-3-(3-METHOXYPHENYL)PROPANOICACID;M-METHOXY-L-PHENYLALANINE;PubChem18018;L-M-TYR(ME);L-Phenylalanine,3-methoxy-;L-PHE(3-OME)-OH;SCHEMBL146611;L-3-METHOXYPHENYLALANINE;CTK4H1380;MolPort-006-665-900;(S)-3-METHOXYPHENYLALANINE;ACT09558;ZINC3679855;ANW-48084;MFCD00044954;AKOS012010733;AB02001
3-Methoxy-L-Phenylalanine is an L-amino acid bearing a methoxy substituent on the aromatic side chain, making it a useful non-standard aromatic building block for peptide and peptidomimetic chemistry. Its side-chain electronics and steric profile differ from phenylalanine, enabling structure-property studies and controlled incorporation into synthetic sequences. As a research-grade amino acid, it is commonly used where an aryl methoxy group is required for downstream binding, conformational effects, or as an intermediate toward substituted aromatic motifs.
1. Peptide Building Block
3-Methoxy-L-Phenylalanine is used as an aromatic amino acid building block for custom peptide synthesis, including solution-phase and solid-phase workflows where the methoxy-bearing phenyl side chain is needed at defined positions. Peptide chemists incorporate it to probe how an O-methoxy substituent influences local environment, aromatic interactions, and physicochemical properties such as polarity and hydrogen-bonding patterns relative to unsubstituted phenylalanine. This makes it a practical choice for preparing modified peptide standards, SAR peptides, and mechanistic peptide probes that require a specific substituted aromatic residue.
2. Peptidomimetic SAR Studies
3-Methoxy-L-Phenylalanine supports medicinal chemistry and chemical biology programs focused on structure-activity relationship (SAR) work using peptidomimetics or constrained peptide analogs. Researchers use the methoxy-substituted aromatic side chain to systematically vary electronic and steric features while maintaining an amino acid-derived backbone. In practice, it is selected when the design calls for an aryl ether functionality to tune interactions in binding assays, improve synthetic handle compatibility for further derivatization, or generate analog panels for comparative characterization by LC-MS, HPLC, and bioassay-compatible workflows.
3. Aromatic Intermediate Development
3-Methoxy-L-Phenylalanine is also used as a pharmaceutical intermediate precursor in industrial and development chemistry where substituted aromatic amino acid motifs are required for downstream transformations. Process and synthetic development teams value it as a defined stereochemical starting material for constructing substituted aromatic scaffolds that retain an amino acid-derived functionality through early stages of route development. The methoxy-bearing phenyl side chain provides a convenient point of functional diversification, enabling subsequent preparation of a range of aromatic intermediates used in specialty chemical manufacturing and research material synthesis.
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