2-Methy-DL-Phenylalanine is a substituted phenylalanine analogue featuring an additional methyl substituent on the phenyl side chain, classifying it as a non-natural, non-proteinogenic amino acid within the aromatic amino acid family. The molecule contains both an amino group and a carboxyl group on the α-carbon while bearing a benzyl-like aromatic side chain that bears the extra methyl functionality, and the "DL" designation indicates a racemic mixture of stereochemical forms at the α-center. It is used in peptide and structure-activity studies where altered aromatic sterics and hydrophobic character are introduced, and it can serve as a precursor for preparing more complex amino acid derivatives and labeled or conjugated analogues for chemical biology and analytical method development.
CAT No: CP15603
CAS No:22888-51-3
Synonyms/Alias:2-Amino-3-(o-tolyl)propanoicacid;22888-51-3;2-amino-3-(2-methylphenyl)propanoicacid;2-METHYL-DL-PHENYLALANINE;2-Amino-3-o-tolyl-propionicacid;DL-2-ME-PHE-OH;DL-2-METHYLPHENYLALANINE;2-Methyl-D-phenylalanine;AC1L8WMI;2-Methy-DL-Phenylalanine;AC1Q2EZ5;SCHEMBL43864;CTK8C4729;O-METHYL-DL-PHENYLALANINE;MolPort-001-838-129;1439AB;ANW-72931;AKOS000196578;AKOS016843203;AB09956;AM83411;MCULE-9582945892;VC30801;alpha-Amino-2-methylbenzenepropionicacid;AK-89321
2-Methy-DL-Phenylalanine is a DL (racemic) amino acid analog featuring a methyl-substituted benzyl side chain (α-amino acid with a phenylalanine-like aromatic group). As a non-natural, chiral building block, it is frequently used in medicinal chemistry and peptide/peptidomimetic design to probe how side-chain sterics and hydrophobicity influence structure and reactivity. Its amino and carboxyl functional groups make it a practical intermediate for incorporation into synthetic sequences and for preparing defined standards in structure-activity and analytical studies.
1. Peptidomimetic Building Blocks
2-Methy-DL-Phenylalanine is used by medicinal chemistry and chemical biology teams to construct peptidomimetic scaffolds and analog libraries where side-chain methylation is used to tune steric bulk around a hydrophobic aromatic moiety. Researchers commonly select this racemic material during early-stage structure-activity relationship (SAR) exploration, enabling rapid synthesis of analog series that compare the effect of methyl substitution on conformational preferences and binding-site complementarity. In downstream workflows, it serves as a defined amino acid building block for assembling modified peptides and peptide-like structures used in hit-to-lead optimization and receptor/ligand binding studies.
2. Structure-Activity Relationship Studies
2-Methy-DL-Phenylalanine supports SAR investigations by providing a consistent, chemically defined variant of a phenylalanine-like residue. Medicinal chemistry groups incorporate this analog into lead compounds or into model peptides to systematically evaluate how adding a methyl substituent to the side chain impacts physicochemical properties such as hydrophobic character and local steric environment. Because the product is supplied as a DL mixture, it is often used when the immediate goal is comparative chemistry across multiple analogs, with stereochemical refinement handled later using enantiopure derivatives or chiral separation if required by the project.
3. Pharmaceutical Intermediate Development
2-Methy-DL-Phenylalanine is also used as a specialty intermediate for the synthesis of non-natural amino acid derivatives and related building blocks that feed into larger pharmaceutical and agrochemical development programs. Process and development chemists rely on amino acid analogs like this to generate downstream intermediates with controlled functional-group patterns for further derivatization, including coupling handles and protected forms used in multi-step assembly. In industrial and contract manufacturing contexts, its role is typically to provide a reproducible chiral scaffold precursor for route development, scale-up feasibility studies, and the preparation of defined analog sets for screening campaigns.
4. Analytical Reference Standards
2-Methy-DL-Phenylalanine is employed in analytical method development and reference standard preparation where a non-natural amino acid analog is needed for calibration, identification, or impurity profiling in chemical and peptide-related workflows. Analytical chemists use racemic amino acid standards to verify retention behavior and to support method validation for LC-based assays that monitor amino acid derivatives, peptide hydrolysates, or synthetic intermediates. Defined availability of this specific methyl-substituted phenylalanine analog helps ensure that analytical signals correspond to the exact structural motif present in the materials being characterized.
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