Boc-2,6-Dimethy-L-Phenylalanine is a Boc-protected, sterically hindered phenylalanine derivative in which the phenyl side chain bears methyl substituents at the 2- and 6-positions, while the backbone retains the amino acid framework. The molecule contains a tert-butoxycarbonyl (Boc) protecting group on the amino functionality and a free carboxylic acid group, and the side chain remains hydrophobic and aromatic, with the name indicating an L-configuration at the stereogenic center. As a protected amino acid building block, it is used in peptide synthesis workflows to control chemoselectivity at the amino group and to introduce a bulky, substituted phenylalanine residue for structure-activity studies and the preparation of more complex amino acid and peptide derivatives.
CAT No: CP14104
Boc-2,6-Dimethy-L-Phenylalanine is a Boc-protected, sterically hindered phenylalanine derivative bearing two methyl substituents at the 2,6-positions of the aromatic ring. This non-proteinogenic amino acid building block is commonly used in peptide chemistry where increased side-chain steric bulk can influence local conformation, proteolytic accessibility, and aromatic packing during sequence assembly. The Boc group provides a standard N-protection handle for controlled peptide coupling workflows, making the compound a practical intermediate for generating defined, research-grade peptide structures.
1. Sterically Tuned Peptide Building
Boc-2,6-Dimethy-L-Phenylalanine is used by peptide chemists to introduce a bulky, substituted phenylalanine residue into peptide sequences for structure-function studies and sequence optimization. The 2,6-dimethyl substitution creates a sterically encumbered aromatic side chain that can modulate how neighboring residues pack and how the peptide backbone samples conformations, which is valuable in medicinal chemistry programs developing peptidomimetics, constrained motifs, or SAR-focused analog series. Because the amino group is Boc-protected, it integrates into standard protected-amino-acid workflows used for reproducible segment assembly and library synthesis.
2. Peptidomimetic And SAR Analogues
Boc-2,6-Dimethy-L-Phenylalanine supports medicinal chemistry and chemical biology efforts that require defined peptidomimetic analogues with modified aromatic character. Researchers incorporate this residue to probe how aromatic steric effects and ring substitution patterns affect physicochemical properties and structure-dependent behavior in peptide-like scaffolds. The Boc-protected form is particularly useful for preparing discrete intermediates that can be carried forward into custom peptide synthesis, enabling systematic comparisons across analog panels where the substituted phenylalanine is the controlled variable.
3. Complex Segment Coupling Intermediate
Boc-2,6-Dimethy-L-Phenylalanine is frequently selected as a protected amino acid intermediate for assembling longer, more complex peptide segments where side-chain steric demands can matter. The combination of Boc protection at the amino terminus and the sterically hindered 2,6-dimethyl phenyl side chain makes it a targeted building block for constructing sequences that require precise residue placement and defined substitution patterns. This product is therefore used in custom peptide manufacturing research and academic peptide synthesis labs that prioritize structural fidelity and reliable downstream coupling into peptide fragments.
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