3-Methy-DL-Phenylalanine is a substituted phenylalanine amino acid derivative featuring a benzyl side chain with an additional methyl substituent on the aromatic ring, placing it in the aromatic, non-proteinogenic/unnatural amino acid class. The molecule contains both an amino group and a carboxyl group, and the "DL" designation indicates a racemic mixture of stereoisomers at the alpha carbon, which can affect incorporation behavior in peptide-forming reactions. In peptide chemistry and chemical biology, it is used as a building block for structure-activity studies, side-chain variation in synthetic peptides, and analytical method development where substituted aromatic amino acid residues are required.
CAT No: CP15703
CAS No:5472-70-8
Synonyms/Alias:5472-70-8;2-Amino-3-(m-tolyl)propanoicacid;3-Methy-DL-Phenylalanine;2-amino-3-m-tolyl-propionicacid;3-METHYLPHENYLALANINE;DL-3-ME-PHE-OH;2-amino-3-(3-methylphenyl)propanoicacid;DL-3-METHYLPHENYLALANINE;NSC14793;AC1L5E1A;SCHEMBL42906;AC1Q5S51;CTK8E3667;3-METHYL-DL-PHENYLALANINE;MolPort-003-990-079;2283-42-3;NSC29447;AR-1F4568;NSC-14793;NSC-29447;AKOS000174493;AKOS016843161;AB21660;AM83420;MCULE-1997175050
3-Methy-DL-Phenylalanine is a DL stereochemical mixture of a phenylalanine analog bearing a methyl substituent on the aromatic ring, providing a sterically modified, non-proteinogenic amino acid scaffold for synthetic and SAR-focused work. As an unprotected amino acid derivative, it offers the standard amino acid functional group set (free amino and carboxyl groups) that is commonly leveraged to build substituted peptide analogs and to prepare defined chiral and achiral intermediates for medicinal chemistry programs. Researchers use this compound to introduce a ring-methyl phenylalanine motif that can modulate conformational preferences and physicochemical properties in downstream peptide-like structures.
1. Peptidomimetic Building Blocks
3-Methy-DL-Phenylalanine is widely used as a substituted amino acid building block for the synthesis of peptidomimetics and peptide analogs where a ring-methyl phenylalanine motif is required. Medicinal chemistry and chemical biology groups incorporate this scaffold into short, defined sequences to generate structure-activity relationship (SAR) panels and to compare how aromatic substitution influences properties such as steric bulk and aromatic packing in peptide-like backbones. Because the compound is supplied as a DL mixture, it is particularly practical for library synthesis workflows where racemic material is acceptable for initial screening, and where subsequent resolution or stereochemical refinement can be performed if needed.
2. Pharmaceutical Intermediate Development
3-Methy-DL-Phenylalanine serves as a useful intermediate for preparing substituted amino acid derivatives used in downstream pharmaceutical intermediate manufacturing. Process development and custom synthesis teams often rely on such ring-substituted amino acid scaffolds to access analog series for medicinal chemistry research, including activated amino acid forms, ester/amide derivatives, and protected intermediates that can be carried forward into larger coupling sequences. The presence of both amino and carboxyl functionalities supports straightforward conversion into downstream coupling-ready derivatives, making it a practical starting point when the target chemistry requires an aromatic methyl-substituted phenylalanine core.
3. Chiral Resolution and Derivative Synthesis
3-Methy-DL-Phenylalanine is commonly handled in workflows that involve stereochemical differentiation, including chiral resolution strategies and preparation of stereochemically defined derivatives. Research groups use the DL starting material to generate enantiomerically enriched forms via established resolution approaches, or to prepare stereochemical variants for comparative studies in synthetic chemistry and SAR development. The aromatic methyl substitution provides an additional handle for differentiating analog behavior across enantiomer sets, and the amino acid functional group pattern supports conversion into derivative classes used to support purification, characterization, and subsequent coupling steps in asymmetric or stereocontrolled synthesis programs.
4. Analytical Reference Material
3-Methy-DL-Phenylalanine is also used as a defined substituted amino acid reference in analytical method development and characterization of complex mixtures containing phenylalanine analogs. Analytical chemistry laboratories employ such standards to verify identity and retention behavior in chromatographic workflows and to support method tuning for amino acid derivative panels. In LC-MS or GC-MS method development contexts, the compound provides a chemically specific marker for substituted phenylalanine scaffolds, supporting accurate assignment of related peaks during impurity profiling, reaction monitoring, and characterization of peptide-like intermediates.
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