Cbz-2-Cyano-D-Phenylalanine is a protected, non-natural amino acid derivative featuring a benzyl-protected carboxyl group (Cbz) and a side chain bearing a cyano substituent at the 2-position relative to the amino acid backbone, with the amino stereochemistry specified as D. The molecule contains both an amino functional group and a carboxyl functionality masked as the Cbz ester, while the cyano group on the side chain provides a polar nitrile handle that can influence hydrogen bonding and electronic properties during coupling and subsequent transformations. In peptide chemistry and chemical biology workflows, it is used as a protected amino acid building block for incorporating the cyano-substituted phenylalanine residue into peptides or peptide-related intermediates, supporting structure-activity studies, labeling strategies, and synthetic access to functionalized aromatic amino acid analogues.
CAT No: CP11709
Cbz-2-Cyano-D-Phenylalanine is a D-configuration amino acid derivative in which the α-amino group is protected as a benzyloxycarbonyl (Cbz) carbamate, while the side chain is a benzyl-substituted phenylalanine framework bearing a stereogenic α-carbon and a 2-cyano substituent at the α-position relative to the carboxylate. The molecule contains a carboxylic acid functionality (or acid-equivalent form depending on handling) together with a nitrile group that is electronically and sterically distinct from native amino acid side chains, enabling controlled transformations and stability under peptide coupling conditions. The Cbz protecting group provides orthogonal reactivity, typically removable under hydrogenolysis-compatible conditions, leaving the underlying amino functionality for subsequent peptide bond formation. The combination of chiral center, nitrile handle, and aromatic ring supports stereochemically defined incorporation into peptide-like scaffolds and downstream conversion into amide, heterocycle, or substituted side-chain motifs.
1. Peptide Synthesis
Cbz-2-Cyano-D-Phenylalanine is used in peptide building workflows where a Cbz-protected amino acid precursor is required to control N-terminus protection during coupling. The protected carbamate and carboxyl group enable standard peptide coupling chemistry to form amide bonds while maintaining the D-stereocenter integrity through the coupling and purification sequence. The nitrile functionality can remain intact during many peptide assembly steps, providing a latent electrophilic/functional handle for post-assembly diversification into cyano-to-amide or heterocycle-containing analogs. Peptide synthesis applications can therefore include preparation of cyano-bearing peptide fragments, peptide analogs, and protected intermediates that feed directly into structure-activity relationship studies and scaffold elaboration.
2. Unnatural Amino Acid Incorporation
Cbz-2-Cyano-D-Phenylalanine serves as a chiral unnatural amino acid building block for incorporating a nitrile-bearing stereodefined residue into peptidomimetics and constrained analogs. The D-configuration at the α-carbon supports stereochemical mapping of backbone recognition, while the Cbz-protected amine provides compatibility with iterative protected amino acid strategies used in unnatural residue incorporation. The nitrile group can be retained to probe binding interactions sensitive to polarity and hydrogen-bond acceptor geometry, or converted after assembly to generate substituted side chains that mimic alternative functional groups. Downstream use includes generation of diversified peptide libraries for biochemical research intermediate preparation and molecular scaffold optimization.
3. Side-Chain Functionalization
Cbz-2-Cyano-D-Phenylalanine is applied in synthetic organic chemistry and chemical manufacturing as a nitrile-bearing amino acid intermediate for side-chain derivatization routes. The nitrile group provides a robust handle for transformations such as nucleophilic addition to yield amide derivatives, or for constructing nitrogen-containing heterocycles via controlled cyclization strategies after the Cbz group is removed. The aromatic phenylalanine core and the D-stereocenter allow stereochemically defined products that can be carried forward into higher-complexity intermediates for fine chemical synthesis. Functionalization workflows can thus produce cyano-to-substituted motifs, enabling access to substituted peptide analog residues and processable intermediates for downstream synthesis.
4. Peptidomimetics And SAR
Cbz-2-Cyano-D-Phenylalanine is relevant to peptidomimetic design and structure-activity relationship studies where introduction of a nitrile-bearing residue modulates conformational preferences and interaction patterns. The Cbz-protected amino acid form supports incorporation into peptide-like backbones while controlling N-protection and minimizing side reactions during fragment coupling. The nitrile functionality functions as a polarity element and a synthetic branch point, enabling systematic comparison of cyano-retaining versus cyano-converted analogs in SAR workflows. The resulting cyano-containing peptide analogs can be prepared as research-grade intermediates for iterative SAR synthesis and molecular design programs.
5. Chiral Intermediate For Synthesis
Cbz-2-Cyano-D-Phenylalanine is utilized as a chiral amino acid intermediate in stereoselective synthesis programs requiring D-configured building blocks with orthogonally removable N-protection. The Cbz carbamate provides a stable protecting group during manipulations that may involve activation of the carboxyl group or protection/deprotection of other functionalities in multi-step routes. The presence of both a stereogenic center and a nitrile group supports downstream conversion into chiral, nitrogen-functionalized derivatives that can be used as intermediates for specialty chemical production. Industrial process chemistry can therefore employ this compound to prepare stereodefined cyano-containing amino acid derivatives that feed into further synthetic elaboration and applied product development.
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