2,6-Dimethy-L-Phenylalanine is a naturally derived, proteinogenic amino acid analogue featuring an L-phenylalanine backbone with two methyl substituents at the 2- and 6-positions of the aromatic ring, creating a sterically hindered, substituted phenyl side chain. The molecule contains a free α-amino group and a free carboxyl group and bears the substituted benzyl side chain characteristic of phenylalanine derivatives, with the additional ortho methyl groups modulating aromatic packing and hydrophobicity without introducing new functional groups beyond the methyl substituents. It is used in peptide and protein-structure studies and in synthetic incorporation workflows to probe how steric bulk and altered aromatic environment influence peptide conformation, binding interactions, or structure-activity relationships.
CAT No: CP14101
2,6-Dimethy-L-Phenylalanine is a sterically hindered, nonstandard phenylalanine analog where two methyl groups at the 2- and 6-positions of the aromatic ring modulate side-chain topology while retaining the L-amino acid stereochemistry. This bulky aryl substitution makes it a useful building block for peptide and peptidomimetic design, where aromatic environment, conformational preferences, and local steric effects can be tuned without changing the amino acid backbone. Researchers also use this compound as a chemically defined amino acid intermediate to access substituted aromatic side chains for structure-property studies.
1. Peptide Building Block
2,6-Dimethy-L-Phenylalanine is used as an amino acid building block for custom peptide synthesis and peptidomimetic development, particularly when steric shielding around the aromatic ring is desired. Peptide chemists incorporate this residue into sequence-defined constructs to probe how aromatic crowding affects local folding, helix/turn preferences, and side-chain packing in solution and in solid-state peptide materials. Its L-configuration supports consistent stereochemical placement in peptide analogs used for structure-activity relationship work and for generating defined standards in peptide characterization workflows.
2. Protein Engineering Probes
2,6-Dimethy-L-Phenylalanine is applied in chemical biology and protein engineering studies that rely on defined, noncanonical amino acid substitutions to interrogate aromatic microenvironments within peptide or protein mimics. Researchers use sterically modified phenylalanine analogs to create chemically precise probes for mapping how bulky aromatic side chains influence binding interfaces, local conformational constraints, or interaction geometries in engineered peptide scaffolds. In these workflows, the residue functions as a controlled structural perturbation that helps distinguish steric contributions from electronic effects when comparing analog series.
3. Medicinal Chemistry SAR Intermediate
2,6-Dimethy-L-Phenylalanine serves as a practical intermediate for medicinal chemistry programs developing peptidic or peptidomimetic candidates where substituted aromatic residues are used to tune physicochemical properties and molecular recognition features. Medicinal chemistry teams incorporate this hindered aryl amino acid into analog libraries to systematically evaluate the impact of aromatic sterics on potency proxies, selectivity trends, and metabolic stability hypotheses during lead optimization. Because the compound is a defined chiral amino acid building block, it supports reproducible synthesis of analogs for downstream analytical characterization, including LC-MS profiling and comparative purity/identity checks across SAR batches.
4. Analytical Reference Standards
2,6-Dimethy-L-Phenylalanine is used to prepare chemically defined reference materials and method controls for analytical workflows involving substituted amino acid residues. Analytical chemists and peptide characterization teams employ it as a structural standard for confirming identity and monitoring retention behavior in LC-MS or related chromatographic methods when analyzing peptide digests, degradation products, or synthetic intermediates containing hindered aromatic residues. This application benefits from the compound's well-defined identity as a single chiral, substituted amino acid, enabling consistent calibration or qualification of analytical runs where aromatic sterics can influence fragmentation and chromatographic response.
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