2,5-Dimethy-DL-Phenylalanine is a substituted phenylalanine amino acid featuring a benzyl side chain bearing two methyl substituents at the 2- and 5-positions of the aromatic ring, with a free amino group and a free carboxyl group that define it as an unprotected amino acid derivative of the phenylalanine class. The molecule is specified as DL, indicating a racemic mixture of stereoisomers at the alpha carbon, and the aromatic ring substitution alters side-chain hydrophobicity and steric profile compared with unsubstituted phenylalanine while retaining the standard amino-carboxyl functionality for peptide coupling. In peptide chemistry and chemical biology workflows, it is used as a building block to introduce a sterically and electronically modified phenylalanine residue for structure-activity studies, backbone or side-chain analog libraries, and the preparation of more complex amino acid and peptide derivatives.
CAT No: CP14003
2,5-Dimethy-DL-Phenylalanine is a non-proteinogenic, DL (racemic) phenylalanine analog featuring two methyl substituents at the 2- and 5-positions of the aromatic ring. This sterically and electronically modified amino acid building block is used in medicinal chemistry and peptide/peptidomimetic research where aromatic substitution patterns are leveraged to probe structure-activity relationships, conformational effects, and chemical stability. As a racemate, it is commonly selected for early-stage SAR screening and for synthetic routes that benefit from a readily available chiral-independent starting material.
1. Peptidomimetic SAR Building Block
2,5-Dimethy-DL-Phenylalanine is used as an aromatic-substituted amino acid building block for preparing peptidomimetics and substituted peptide analogs in structure-activity relationship (SAR) studies. Medicinal chemistry groups incorporate this type of ring-disubstituted phenylalanine into short peptides, constrained analogs, or backbone-modified scaffolds to study how ortho and meta methyl substitution patterns influence physicochemical properties and downstream behavior in assay systems. The substituted phenyl ring provides a clear handle for systematic variation of steric bulk and hydrophobic character, supporting comparative library synthesis during lead optimization campaigns.
2. Peptide Analog Synthesis
2,5-Dimethy-DL-Phenylalanine serves as a practical component for assembling peptide analogs and non-natural peptide segments in custom peptide synthesis workflows. Research groups use this racemic amino acid when the immediate goal is to generate a set of substituted analogs for screening, where separating enantiomers is deferred until later development stages. The amino acid's phenylalanine backbone enables straightforward incorporation into peptide-like structures, while the 2,5-dimethyl aromatic motif helps differentiate these analogs from standard phenylalanine-containing references used in parallel control experiments.
3. Pharmaceutical Intermediate Development
2,5-Dimethy-DL-Phenylalanine is also used as a specialty intermediate precursor for downstream synthesis of substituted aromatic fragments and chiral-independent analogs relevant to medicinal chemistry programs. Process and R&D chemists select this building block when they need an amino acid-derived scaffold bearing a defined, methylated aromatic substitution pattern to enable rapid derivatization into protected intermediates, coupling-ready derivatives, or further functionalized aromatic systems. Its DL nature can simplify early synthetic planning for library generation and comparative chemistry, particularly when the stereochemical outcome is addressed later by resolution or stereospecific steps if required.
4. Analytical Reference Material
2,5-Dimethy-DL-Phenylalanine is used in analytical method development and reference preparation where substituted phenylalanine analogs are required as standards. Analytical chemistry teams employ this compound to support LC-MS or related workflows that monitor non-natural amino acid incorporation, quantify synthetic intermediates, or verify identity and purity trends across peptide analog series. The defined 2,5-dimethyl substitution pattern makes it a useful discriminating standard against unsubstituted phenylalanine and other aromatic variants, enabling clearer interpretation of chromatographic and mass spectral results during research synthesis and characterization.
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