3-Methy-D-Phenylalanine is a non-proteinogenic, D-configured phenylalanine analogue featuring a benzyl side chain bearing an additional methyl substituent at the meta position, along with a free amino group and a free carboxyl group on the α-carbon. The molecule contains the characteristic amino acid backbone (α-amino and α-carboxyl functionalities) while the substituted aromatic side chain modulates hydrophobicity and steric profile relative to unsubstituted phenylalanine, enabling stereochemically defined incorporation into peptide analogues. It is used in peptide chemistry and chemical biology workflows such as structure-activity studies, substrate analogue preparation for enzyme-substrate assays, and the synthesis of modified peptides for conformational or interaction mapping.
CAT No: CP15702
CAS No:114926-39-5
Synonyms/Alias:(R)-2-Amino-3-(m-tolyl)propanoicacid;114926-39-5;D-3-Methylphenylalanine;3-Methy-D-Phenylalanine;(2R)-2-amino-3-(3-methylphenyl)propanoicacid;D-3-METHYLPHE;3-Methyl-D-phenylalanine;(R)-2-amino-3-m-tolylpropanoicacid;PubChem18697;AC1ODU3O;D-3-ME-PHE-OH;D-PHE(3-ME)-OH;H-D-PHE(3-ME)-OH;SCHEMBL1795728;M-METHYL-D-PHENYLALANINE;MolPort-001-758-743;D-PHENYLALANINE,3-METHYL-;ZINC1653229;ANW-72945;AB10080;AM83419;OR14701;AJ-28839;AK109277;AM003066
3-Methy-D-Phenylalanine is a D-configured, non-proteinogenic amino acid bearing a benzyl side chain with an additional methyl substituent (α-methyl substituted aromatic side chain). This sterically defined, chiral aromatic residue is used as a building block to introduce conformational and steric modulation into peptide and peptidomimetic structures, supporting structure-activity relationship studies and medicinal chemistry optimization. Its non-natural stereochemistry makes it particularly valuable when researchers need to control backbone/side-chain presentation rather than rely on proteinogenic amino acids.
1. Peptidomimetic Building Block
3-Methy-D-Phenylalanine is used by medicinal chemistry and peptide chemistry groups to construct peptidomimetics and constrained peptide analogs where the D-configuration and the extra methyl group on the aromatic side chain help tune sterics and local conformational preferences. In practice, it is incorporated into custom peptide sequences during lead optimization to probe how altered side-chain bulk and chirality affect properties such as binding-site complementarity and overall scaffold behavior in structure-activity relationship workflows. Researchers commonly select this residue when they want a non-natural aromatic amino acid that differs from standard phenylalanine derivatives while remaining straightforward to position as a single, defined stereocenter within a larger synthetic sequence.
2. Peptide Synthesis For SAR
3-Methy-D-Phenylalanine serves as a targeted amino acid building block for solid-phase peptide synthesis and solution-phase assembly in structure-activity relationship studies, especially when a D-amino acid is intentionally introduced to modulate stereochemical patterning along the peptide backbone. Peptide developers use this residue to generate analog panels that systematically vary aromatic side-chain substitution and stereochemistry, enabling comparative evaluation of how each modification impacts downstream assay readouts. Because the side chain is an aromatic benzyl system with added methyl substitution, it offers a distinct steric/electronic profile that is useful for mapping SAR trends in lead series where phenylalanine-like motifs are being refined.
3. Chiral Intermediate For Medicinal Chemistry
3-Methy-D-Phenylalanine is also used as a chiral intermediate in the preparation of non-natural amino acid derivatives and specialized fragments for medicinal chemistry programs. Synthetic teams employ it to access stereochemically defined building blocks that can be further functionalized into protected amino acid derivatives, coupling-ready forms, or scaffold components for larger heterocycle- and peptidomimetic-focused synthesis campaigns. The D-stereochemistry and the methyl-substituted aromatic side chain provide a controlled stereochemical handle that is valuable when maintaining chirality throughout multistep development is critical for producing well-defined analogs for screening and analytical characterization.
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