Cbz-2,4-Dimethy-D-Phenylalanine is a Cbz-protected, non-proteinogenic amino acid derivative featuring a substituted phenyl side chain with two methyl substituents at the 2- and 4-positions and a stereochemically specified D-configuration at the alpha carbon. The molecule contains a free carboxyl group and an N-terminus protected as a benzyloxycarbonyl (Cbz) carbamate, which masks the amino functionality while preserving the carboxyl group for coupling chemistry. In peptide and amino acid derivative synthesis, it is employed as a protected building block to introduce the dimethylated, D-phenylalanine-like side chain into analogs for structure-activity studies, conformational probing, and chemical biology labeling where a defined aromatic substitution pattern is required.
CAT No: CP13909
Cbz-2,4-Dimethy-D-Phenylalanine is a D-configuration, Cα-disubstituted phenylalanine derivative bearing a benzyloxycarbonyl (Cbz) protecting group on the amino function and a free carboxyl group suitable for peptide coupling chemistry. The 2,4-dimethyl substitution pattern on the aromatic side chain framework increases steric bulk around the stereogenic center, while the D stereochemistry provides defined chiral control for downstream stereoselective synthesis. The Cbz carbamate can be removed under hydrogenolysis conditions, enabling orthogonal protection strategies when constructing peptide sequences or assembling peptidomimetic scaffolds. The combination of an N-protected amino acid and a carboxylic acid establishes a practical reactivity profile for amide bond formation, derivative generation, and chiral intermediate preparation in fine chemical and biochemical research workflows.
1. Peptide Synthesis
Cbz-2,4-Dimethy-D-Phenylalanine is used in peptide building block preparation where the Cbz-protected amine and free carboxylic acid enable controlled peptide coupling to form amide linkages. The D-configuration at the α-carbon and the 2,4-dimethyl substitution pattern can be leveraged to tune conformational preferences and steric environments within oligopeptides and peptide analogs. Cbz protection supports stepwise solid-phase or solution-phase assembly, followed by deprotection to reveal the amine for subsequent coupling cycles. The resulting D-amino acid incorporation supports construction of stereochemically defined sequences for peptide science and synthetic methodology development.
2. Peptidomimetics Design
Cbz-2,4-Dimethy-D-Phenylalanine is applied in peptidomimetic construction where the bulky, chiral amino acid side-chain environment contributes to binding-site shape complementarity and protease-resistance-oriented scaffold design. The protected carbamate and carboxylic acid functionality facilitate conversion into amide-linked fragments that can be incorporated into constrained analogs or hybrid peptide/heterocycle architectures. Cbz deprotection can be paired with orthogonal protecting groups on other residues to support iterative assembly of peptidomimetic libraries. Downstream derivatives may serve as chiral fragments for molecular design studies and structure-activity relationship investigations requiring defined D-amino acid stereochemistry.
3. Chiral Synthesis Intermediate
Cbz-2,4-Dimethy-D-Phenylalanine functions as a chiral amino acid intermediate for stereoselective synthesis routes that require a D-configured, N-protected phenylalanine derivative. The presence of a Cbz carbamate provides a stable handle for protecting-group management during transformations that target the carboxyl group for activation, esterification, or further derivatization. The 2,4-dimethyl substitution pattern can be exploited to generate sterically biased analogs that propagate stereochemical information into downstream chiral products. The compound can be employed to prepare labeled or functionalized amino acid derivatives that maintain the D stereocenter through subsequent coupling and deprotection steps.
4. Side-Chain Functionalization
Cbz-2,4-Dimethy-D-Phenylalanine is suitable for side-chain functionalization workflows in synthetic organic chemistry where the aromatic framework and methyl-substituted pattern enable targeted derivatization strategies. The Cbz-protected amine allows selective manipulation of the carboxyl group and side-chain substituents without uncontrolled amide formation, supporting sequential intermediate construction. Carboxyl activation and subsequent transformations can generate amide, ester, or activated acid derivatives that serve as precursors for conjugation handles or further scaffold elaboration. The stereochemically defined D amino acid core supports downstream generation of functionalized chiral molecules used in chemical biology research intermediate preparation and specialty fine chemical synthesis.
5. Pharmaceutical Manufacturing
Cbz-2,4-Dimethy-D-Phenylalanine is applicable to pharmaceutical manufacturing as a protected amino acid input for producing D-amino acid-containing intermediates used in peptide-like active ingredient synthesis. The Cbz carbamate provides a robust N-protection strategy compatible with common peptide coupling chemistries, while the free carboxylic acid supports conversion into activated intermediates for controlled amide bond formation. Hydrogenolysis-ready Cbz deprotection can be integrated into manufacturing sequences that require orthogonal protection and predictable deprotection timing. The resulting D-amino acid derivatives can feed into larger-scale peptidomimetic or peptide intermediate generation, supporting process chemistry and specialty chemical production where stereochemical integrity is required.
6. Analytical Standards Development
Cbz-2,4-Dimethy-D-Phenylalanine can be employed in analytical research as a chiral amino acid standard or reference intermediate for method development involving protected amino acids and D-residue-containing products. The defined Cbz protection state and D stereochemistry provide a distinguishable chemical signature for chromatographic and spectrometric characterization of peptide coupling intermediates, deprotection products, and stereochemical impurities. The carboxylic acid functionality supports derivatization into detectable forms when developing assays for amino acid derivative profiling. The compound's structural specificity makes it suitable for quality control-oriented analytical workflows in peptide science, synthetic methodology verification, and biochemical research intermediate monitoring.
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