3-Methy-L-Phenylalanine is a substituted, naturally derived amino acid analogue in which the phenylalanine side chain bears an additional methyl substituent, retaining the amino acid backbone with a primary amino group and a carboxyl group. The molecule is presented in the L stereochemical form as indicated by the name, and its aromatic side chain provides a hydrophobic, π-interacting functionality that can be used to probe how steric and electronic changes on the phenyl ring affect peptide or protein structure. As a free amino acid building block, it can be employed in peptide synthesis and structure-activity studies to introduce a defined aromatic methyl substitution for comparative analysis of conformational behavior, binding interactions, or labeling strategies in chemical biology workflows.
CAT No: CP15701
CAS No:114926-37-3
Synonyms/Alias:3-Methyl-L-phenylalanine;114926-37-3;L-3-Methylphenylalanine;3-Methy-L-Phenylalanine;3-Methylphenyl-L-alanine;(S)-2-Amino-3-(m-tolyl)propanoicacid;L-3-METHYLPHE;(2S)-2-amino-3-(3-methylphenyl)propanoicacid;3-METHYLPHENYLALANINE;(S)-2-amino-3-m-tolylpropanoicacid;DL-3-METHYLPHENYLALANINE;b-(m-tolyl)alanine;PubChem18698;(R)-b-(m-tolyl)alanine;(S)-3-methylphenylalanine;AC1MC52V;L-3-ME-PHE-OH;SCHEMBL42907;H-PHE(3-ME)-OH;L-PHE(3-ME)-OH;M-METHYL-L-PHENYLALANINE;CTK4F0302;JZRBSTONIYRNRI-VIFPVBQESA-N;MolPort-001-758-744;2283-42-3
3-Methy-L-Phenylalanine is a branched, proteinogenic-analog amino acid featuring a methyl-substituted side chain on the L-phenylalanine scaffold. This structural modification preserves the aromatic character while introducing steric and hydrophobic changes that are useful for studying how side-chain shape influences peptide conformation, binding, and processing. In research workflows, it is typically handled as a chiral amino acid building block for incorporation into synthetic peptides and as a defined stereochemical reference for structure-property investigations.
1. Peptide Building Block
3-Methy-L-Phenylalanine is used by peptide chemists to introduce a methyl-branched aromatic residue into custom peptide sequences. Its L-configuration and aromatic side chain make it a practical tool for probing how subtle steric bulk affects local structure, helix/turn preferences, and conformational bias in short peptides and peptidomimetics. This amino acid building block is commonly selected for SAR-style peptide optimization where maintaining an aromatic pharmacophore while tuning side-chain geometry is important for downstream binding or stability studies.
2. Protein Engineering Probes
3-Methy-L-Phenylalanine is applied in chemical protein engineering and protein research settings where defined, non-native residues are incorporated into peptide segments or used to model side-chain effects in protein-interaction studies. Researchers use it to generate modified peptides that mimic or perturb aromatic microenvironments, enabling controlled comparisons against reference phenylalanine-containing analogs in binding assays, structural studies, and protease/processing experiments performed with synthetic substrates. The methyl branching provides a targeted way to vary steric packing around aromatic sites without changing the overall hydrophobic character.
3. Pharmaceutical Intermediate Development
3-Methy-L-Phenylalanine serves as a chiral intermediate for medicinal chemistry programs that require incorporation of branched aromatic amino acid motifs into larger, bioactive scaffolds. Process and development teams use this defined stereochemical building block to prepare amino acid-derived fragments for peptide-like drug candidates, peptidomimetic leads, and SAR libraries where side-chain sterics are tuned to influence target engagement and off-target interactions. Its amino acid functionality supports straightforward conversion into downstream coupling-ready forms used in custom peptide synthesis and fragment assembly workflows.
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