Cbz-2-Methy-D-Phenylalanine is a Cbz-protected, non-natural amino acid derivative featuring a phenylalanine backbone bearing a 2-methyl substitution on the alpha carbon and a D-stereochemical configuration as indicated by the name. The molecule contains an N-terminal benzyloxycarbonyl (Cbz) carbamate that masks the amino functionality while retaining a free carboxylic acid for subsequent coupling, and its side chain presents a substituted benzyl group consistent with hydrophobic aromatic character. In peptide and amino-acid derivative synthesis, this protected analogue is used as a building block in stepwise assembly or labeling workflows where controlled chemoselectivity of the carboxyl group and protection of the amino group are required.
CAT No: CP15609
Cbz-2-Methy-D-Phenylalanine is a Cbz-protected, D-configured phenylalanine derivative bearing a stereogenic center at the alpha position and an additional methyl substituent at C-2, which together define a rigid chiral framework for stereocontrolled peptide chemistry. The molecule contains a benzyloxycarbonyl (Cbz) carbamate on the amino functionality and a carboxylic acid group, enabling conversion into peptide coupling partners while maintaining orthogonal protection behavior during multi-step syntheses. The D-configuration and 2-methyl substitution influence conformational preferences and steric environment around the amide-forming site, which can affect coupling selectivity and subsequent transformations. Aromatic side-chain functionality and the protected amine also support downstream derivatization, including formation of amide-linked intermediates and controlled deprotection to reveal a reactive amino group for stepwise assembly.
1. Peptide Synthesis
Cbz-2-Methy-D-Phenylalanine is employed in peptide building workflows where a Cbz-protected amino acid provides a stable N-protection handle during coupling and chain extension. The carbamate-protected amine and free carboxylic acid enable standard peptide coupling chemistry to form amide bonds while preserving the D-stereocenter and the 2-methyl substitution that can modulate local sterics in the growing sequence. Cbz protection supports iterative synthesis cycles and can be removed under deprotection conditions compatible with sensitive side-chain motifs present in the target peptide. Resulting D-2-methyl phenylalanine residues are used to construct peptide analogs with defined stereochemistry for structure-function studies and synthetic methodology development in amino acid chemistry.
2. Peptidomimetics And SAR Studies
Cbz-2-Methy-D-Phenylalanine is suitable for peptidomimetic design and structure-activity relationship studies that require incorporation of a non-natural, sterically modified amino acid residue. The D-configuration and alpha,alpha-disubstitution pattern (2-methyl plus the chiral center) can tune backbone conformation and side-chain presentation when translated into amide-linked scaffolds. The aromatic side chain supports hydrophobic and π-interaction contributions, while the protected amine allows controlled integration into larger molecular frameworks without premature reactivity. Downstream, deprotection and subsequent coupling can generate defined analog series for SAR investigations using amino acid derivative libraries and fragment-based scaffold refinement.
3. Chiral Amino Acid Intermediate
Cbz-2-Methy-D-Phenylalanine serves as a chiral amino acid intermediate for stereodefined synthesis of D-configured building blocks used across asymmetric and chiral pool-inspired routes. The Cbz carbamate provides an orthogonal protection strategy that can be maintained through derivatization steps, while the carboxylic acid enables conversion to activated ester or coupling-ready forms for downstream assembly. The presence of both a stereogenic alpha center and the 2-methyl substituent makes the compound a useful reference material for controlling stereochemical outcomes in subsequent peptide coupling or functional group transformations. Chiral intermediate utilization can extend to manufacturing of fine chemicals where consistent stereochemical identity is required for reproducible downstream product formation.
4. Side-Chain Functionalization
Cbz-2-Methy-D-Phenylalanine can be applied to side-chain functionalization strategies that generate substituted aromatic analogs while retaining the protected amino acid framework for sequential synthesis. The aromatic phenyl side chain can participate in electrophilic substitution or coupling-based modifications after appropriate activation or protection management, enabling access to substituted phenylalanine derivatives used in chemical biology and materials-oriented research. The Cbz-protected amine helps isolate the nitrogen functionality from conditions used to modify the aromatic ring, supporting chemoselective transformation planning. Resulting functionalized amino acid derivatives can be incorporated into peptide-like constructs or used as intermediates for generating bioactive-mimetic structures and analytical standards.
5. Chemical Manufacturing Intermediate
Cbz-2-Methy-D-Phenylalanine is relevant to process chemistry and specialty chemical production as a protected amino acid intermediate with a clear protection/deprotection logic for stepwise manufacturing routes. The Cbz carbamate provides a stable N-protection group during coupling operations and can be removed to expose the amino functionality for subsequent manufacturing stages, including formation of peptide intermediates or further derivatization. The free carboxylic acid supports conversion into process-compatible activated forms, facilitating controlled assembly of amide-containing products in a reproducible manner. Industrially, the stereodefined D-2-methyl phenylalanine residue can be used to produce defined peptidic or peptidomimetic intermediates for downstream synthesis in fine chemical and biochemical research supply chains.
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