Cbz-3-Cyano-L-Phenylalanine is a Cbz-protected, L-phenylalanine-derived amino acid derivative bearing a cyano substituent at the 3-position of the aromatic side chain. The molecule contains a free carboxyl group and an N-terminus protected as a benzyloxycarbonyl (Cbz) carbamate, with the aromatic ring presenting a nitrile functional handle while retaining the stereochemical form indicated by "L." In peptide chemistry, this protected amino acid is used as a building block for introducing an aryl nitrile side chain into peptides or peptide-like structures, supporting structure-activity studies and analytical labeling strategies that rely on the cyano functionality.
CAT No: CP11808
Cbz-3-Cyano-L-Phenylalanine is a Cbz-protected L-phenylalanine derivative bearing a stereochemically defined alpha-amino acid framework and a 3-cyano substituent on the phenyl side chain. The molecule contains a carbamate (Cbz) on nitrogen and a carboxylic acid functionality, providing complementary reactivity for peptide coupling after standard deprotection or activation strategies. The aromatic ring with an electron-withdrawing nitrile group modulates side-chain polarity and can influence conformational preferences during peptide assembly and subsequent derivatization. The combination of a stable N-protecting group, a chiral center, and a nitrile handle makes the compound a practical chiral amino acid intermediate for constructing functionalized peptide building blocks and downstream synthetic targets.
1. Peptide Synthesis
Cbz-3-Cyano-L-Phenylalanine is used in peptide building block preparation and solid-phase or solution-phase peptide synthesis workflows where controlled N-protection and defined stereochemistry are required. The Cbz carbamate protects the alpha-amino group during coupling, while the carboxylic acid participates in amide bond formation after activation. The 3-cyano-substituted phenyl side chain can be retained through peptide assembly to introduce a nitrile-bearing aromatic residue into peptide analogs for conformational and electronic tuning. The resulting peptide products can serve as substrates for further side-chain transformations or as defined structural probes in amino acid chemistry and peptide science.
2. Side-Chain Functionalization
Cbz-3-Cyano-L-Phenylalanine is applicable to side-chain functionalization strategies that leverage the nitrile as a chemically addressable functional group. The electron-withdrawing nitrile on the aromatic ring can undergo conversion to more reactive or polar functionalities under appropriate synthetic conditions, enabling access to amide, carboxamide, or heteroatom-containing derivatives while preserving the L-configuration at the alpha carbon. The Cbz-protected amine supports orthogonal protection logic, allowing selective deprotection and subsequent coupling or derivatization steps in multi-intermediate sequences. Downstream products may include nitrile-to-functional-group analogs used in structure-activity relationship studies, peptidomimetic construction, and synthetic organic chemistry route development.
3. Chiral Amino Acid Intermediate
Cbz-3-Cyano-L-Phenylalanine is suitable as a chiral amino acid intermediate for stereoselective synthesis programs that require an L-configured backbone with a stable N-protecting group. The defined stereocenter and the Cbz carbamate enable reproducible handling during intermediate preparation, while the aromatic nitrile substituent provides a functional handle for later diversification. The compound can be employed in the synthesis of chiral fragments that incorporate nitrile-bearing phenylalanine-like motifs into larger molecules, including constrained peptide analogs and amino acid-derived scaffolds. The combination of chiral control and orthogonal functional group compatibility supports process chemistry intermediate design and fine chemical synthesis where modular assembly is needed.
4. Chemical Biology Probes
Cbz-3-Cyano-L-Phenylalanine is utilized in chemical biology research where residue-level modifications can tune molecular recognition and physicochemical properties of peptide or protein-binding ligands. The nitrile-bearing aromatic side chain can serve as a stable polar substituent that affects hydrogen-bonding patterns and dipole characteristics without requiring immediate conversion to a reactive electrophile. The Cbz-protected amino acid framework facilitates incorporation into labeled or modified peptide constructs through standard peptide coupling chemistry, enabling generation of structured chemical probes for biochemical investigation. The resulting nitrile-containing biomolecular derivatives can be used to interrogate binding modes, conformational effects, and side-chain electronics in amino acid and peptide-based molecular design.
5. Pharmaceutical Manufacturing Intermediates
Cbz-3-Cyano-L-Phenylalanine is relevant to pharmaceutical manufacturing and specialty chemical production contexts that require well-defined protected amino acid building blocks for controlled synthesis of peptide-like intermediates. The Cbz group provides a robust protection strategy for the alpha-amino functionality during activation and coupling steps, supporting reliable intermediate handling in multi-step manufacturing sequences. The nitrile-substituted phenylalanine residue can be carried forward into drug discovery candidates or process intermediates where later functional group conversion is planned, including transformation to carboxamide-type motifs. The compound's structural features align with industrial intermediate preparation needs for stereochemically consistent amino acid derivatives and downstream peptidomimetic or peptide-analog manufacturing.
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