Cbz-3,5-Dimethy-D-Phenylalanine is a Cbz-protected, non-natural amino acid derivative featuring a phenylalanine backbone bearing two methyl substituents at the 3 and 5 positions of the aromatic side chain and a stereochemical designation of D. The molecule contains an N-Cbz carbobenzyloxy protecting group on the amino functionality and a free carboxyl group, while the dimethylated benzyl side chain provides increased steric bulk and hydrophobic character relative to unsubstituted phenylalanine. It is used in amino acid and peptide synthesis workflows as a protected building block that controls amine chemoselectivity during coupling steps and supports the preparation of modified peptide analogues for structure-activity studies, chemical biology labeling, or analytical method development.
CAT No: CP14309
Cbz-3,5-Dimethy-D-Phenylalanine is a D-configuration phenylalanine derivative bearing a benzyloxycarbonyl (Cbz) carbamate on the amino group and a sterically enriched aromatic side-chain substituted at the 3,5-positions with two methyl groups. The molecule combines a chiral α-carbon with a protected primary amine, a free carboxylic acid or acid-equivalent functionality depending on the supplier form, and an aromatic ring whose increased hydrophobicity and steric bulk can modulate conformational preferences in peptide contexts. The Cbz group supports standard peptide coupling workflows by remaining stable under many coupling conditions while enabling controlled deprotection via hydrogenolysis or acidolysis strategies. The D-stereochemistry makes it a stereochemically defined building block for preparing D-amino acid-containing peptides and chiral intermediates used in mechanistic studies, peptidomimetics, and asymmetric synthesis planning.
1. Peptide Synthesis
Cbz-3,5-Dimethy-D-Phenylalanine is used in peptide coupling chemistry to introduce a D-amino acid residue with a bulky, 3,5-dimethyl-substituted phenyl side chain. The Cbz-protected amine reduces side reactions during activation and coupling, while the D-configuration provides stereochemical control for generating peptide sequences with defined backbone chirality. The aromatic side-chain can influence local packing and protease recognition patterns in peptide analogs, supporting structure-directed peptide assembly. Downstream, the residue can be incorporated into protected peptide fragments and later deprotected to yield D-phenylalanine-containing peptides for research-grade scaffold generation and method development in amino acid chemistry.
2. Peptidomimetics And SAR
Cbz-3,5-Dimethy-D-Phenylalanine is applied in peptidomimetic construction and structure-activity relationship studies where D-amino acid incorporation and side-chain sterics are used to tune molecular recognition. The combination of a protected carbamate (Cbz) and a stereodefined D-α-center enables systematic variation of peptide-like scaffolds while maintaining compatibility with common protecting-group strategies during iterative synthesis. The 3,5-dimethyl-substituted phenyl ring can affect hydrophobic contact patterns and steric shielding around the residue, supporting SAR mapping of conformational and binding determinants. The resulting D-residue-containing analogs can serve as intermediates for generating libraries of peptide mimetics and for comparative evaluation of structure-driven properties in biochemical research workflows.
3. Chiral Building Block Intermediate
Cbz-3,5-Dimethy-D-Phenylalanine functions as a chiral amino acid intermediate for stereoselective synthesis planning and downstream derivatization of D-phenylalanine motifs. The D-configuration at the α-carbon provides a fixed stereochemical handle for preparing enantiopure intermediates used in asymmetric synthesis, fragment elaboration, and chiral auxiliary-free routes. The Cbz protection can be retained through multiple transformations and then removed under controlled conditions to expose the amine for further coupling, labeling, or functional group installation. The sterically substituted aromatic side chain can also serve as a robust scaffold element for creating chiral small molecules and peptide-derived fragments used in molecular design and synthetic methodology development.
4. Chemical Biology Labeling
Cbz-3,5-Dimethy-D-Phenylalanine is suitable for chemical biology applications that require incorporation of a D-amino acid residue into labeled or functionalized peptide constructs. The protected amine allows controlled assembly of conjugation-ready peptide intermediates, while subsequent deprotection can enable attachment of linkers, dyes, affinity tags, or bioorthogonal handles depending on the chosen downstream chemistry. The hydrophobic, sterically hindered 3,5-dimethyl phenyl side chain can modulate solubility and local environment around the labeling site, which may be relevant for maintaining structural integrity of peptide probes. The compound therefore supports preparation of peptide-based reagents used for biomolecular interaction studies, receptor binding assays, and analytical probe generation where stereochemistry and side-chain architecture are key variables.
5. Pharmaceutical Intermediate Preparation
Cbz-3,5-Dimethy-D-Phenylalanine is utilized as a protected amino acid building block in pharmaceutical intermediate preparation for manufacturing-oriented peptide and peptidomimetic fragments. The Cbz carbamate provides a stable N-protection strategy compatible with standard peptide coupling and intermediate handling, supporting scalable synthesis of protected D-amino acid sequences. The defined D-stereochemistry and bulky aromatic side chain enable consistent incorporation into drug-like peptide analogs and related fine chemicals where stereochemical fidelity is required for reproducible downstream properties. The compound can be carried through protected synthetic sequences and then converted to the corresponding free amine or further functionalized intermediates for integration into larger synthetic routes used in specialty chemical production and process chemistry.
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