Boc-2,6-Dimethy-D-Phenylalanine is a protected, non-natural amino acid derivative featuring a phenylalanine backbone bearing 2,6-dimethyl substitution on the aromatic ring and a Boc-protected amino group. The molecule contains a free carboxylic acid and a stereochemically specified D-configuration at the alpha carbon, while the Boc group on the nitrogen functions as an amine protecting group to control chemoselectivity during stepwise peptide coupling. It is used as a building block in peptide synthesis and structure-activity studies where sterically modified, aromatic side-chain functionality is required for preparing more complex amino acid and peptide derivatives.
CAT No: CP14105
Boc-2,6-Dimethy-D-Phenylalanine is a Boc-protected, D-configured phenylalanine derivative bearing two methyl substituents at the 2 and 6 positions of the aromatic ring. This sterically enriched, non-natural amino acid building block is used to introduce bulky, conformationally biasing side-chain environments into peptides and peptidomimetics during medicinal chemistry and structure-activity relationship studies. Its protected α-amino group makes it a practical intermediate for stepwise peptide assembly and for preparing defined analogs where aromatic substitution pattern and stereochemistry are critical.
1. Peptide Analog Synthesis
Boc-2,6-Dimethy-D-Phenylalanine is used by custom peptide synthesis groups and medicinal chemistry teams to incorporate a sterically hindered, substituted aromatic residue into defined peptide analogs. The 2,6-dimethyl substitution pattern on the phenyl side chain provides a distinct steric and hydrophobic profile compared with unsubstituted phenylalanine, enabling SAR-driven comparisons in lead optimization programs. The Boc protection supports its handling and coupling as a protected amino acid building block in stepwise assembly workflows used to generate small peptide libraries and analog series for downstream biological evaluation.
2. Peptidomimetic Structure Studies
Boc-2,6-Dimethy-D-Phenylalanine is frequently selected in chemical biology and peptidomimetic development to probe how aromatic bulk and D-stereochemistry influence peptide conformation and local side-chain packing. Researchers use this residue to create analogs with controlled steric demand at the side-chain aromatic ring, supporting mechanistic studies of structure-function relationships in receptor-binding motifs, enzyme recognition elements, or scaffold-stabilizing segments. Defined incorporation of this substituted phenylalanine derivative helps isolate the contribution of aromatic substitution and stereochemical configuration in comparative studies across closely related analogs.
3. Pharmaceutical Intermediate Development
Boc-2,6-Dimethy-D-Phenylalanine serves as a practical protected amino acid intermediate for downstream synthesis of non-natural peptide fragments and pharmaceutical-grade building blocks used in process chemistry. Development teams use it to prepare specific D-amino acid-containing segments where the substituted aromatic ring is required to match a target molecular design. The Boc-protected form supports modular intermediate manufacturing strategies, allowing controlled assembly of complex peptidomimetic structures while maintaining the defined stereochemical and side-chain substitution features through the synthetic sequence.
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