Cbz-2-Cyano-L-Phenylalanine is a Cbz-protected, L-configured amino acid derivative in which the phenylalanine side chain is retained while the alpha position bears a cyano substituent, classifying it as a substituted aromatic amino acid building block for peptide-related synthesis. The molecule contains a carboxyl group masked as a protected functionality via the benzyloxycarbonyl (Cbz) protecting group on the amino functionality, alongside a free or protected carboxyl terminus depending on the supplied form, and features a nitrile side substituent that provides a polar, non-ionizable handle for structure-property studies. In synthetic chemistry and chemical biology workflows, this protected cyano-bearing analogue is employed as a controlled-residue precursor to introduce the 2-cyano substitution into peptides or peptide intermediates, supporting studies of side-chain electronics, backbone substitution effects, and analytical method development for modified amino acid incorporation.
CAT No: CP11708
Cbz-2-Cyano-L-Phenylalanine is an N-Cbz protected L-phenylalanine derivative bearing a stereogenic alpha-carbon substituted with a cyano group at the 2-position and a phenyl side chain. The molecule combines a carbamate-protected amino functionality with a nitrile-bearing backbone, yielding a robust chiral amino acid intermediate that can participate in peptide coupling after appropriate activation. The Cbz group provides a stable protecting strategy under many peptide synthesis conditions while enabling controlled deprotection to regenerate the free amine for subsequent transformations. The nitrile and aromatic phenyl substituent contribute distinct polarity and electrophile/functionalization handles, supporting downstream conversion into amide, heterocycle, or side-chain-modified analogs used in synthetic organic chemistry and peptide science.
1. Peptide Synthesis
Cbz-2-Cyano-L-Phenylalanine serves as a protected amino acid building block for peptide coupling chemistry in research and fine chemical synthesis. The N-Cbz carbamate protects the amino group during activation of the carboxyl functionality, while the L-configuration at the alpha-carbon supports stereochemically defined incorporation into peptide chains. The 2-cyano substituent can remain intact through standard coupling/deprotection sequences or be carried forward as a latent functional group for later derivatization of the resulting peptide or peptidomimetic scaffold. Downstream use includes preparation of cyano-containing peptide analogs for structure-activity relationship studies and synthetic method development in peptide construction.
2. Peptidomimetics And SAR
Cbz-2-Cyano-L-Phenylalanine is suitable for peptidomimetic construction where a nitrile-bearing amino acid residue provides a defined electronic and hydrogen-bonding profile. The cyano group at the alpha-position functions as a conformationally and electronically informative substituent that can influence backbone interactions, while the phenyl side chain maintains aromatic recognition features typical of phenylalanine-derived scaffolds. N-Cbz protection supports sequential assembly of analogs and controlled deprotection to enable further functionalization or conjugation steps. Resulting cyano-substituted peptide analogs can be applied in SAR studies and molecular design workflows that require stereochemically precise amino acid incorporation.
3. Chiral Amino Acid Intermediate
Cbz-2-Cyano-L-Phenylalanine functions as a chiral amino acid intermediate for stereoselective synthesis of functionalized derivatives in process chemistry and specialty chemical production. The combination of an L-stereocenter with a nitrile handle enables conversion to downstream amide, amidine, or heterocycle-forming intermediates while maintaining the stereochemical integrity established at the amino acid stage. The Cbz carbamate protecting group provides a chemically addressable site for controlled deprotection, allowing the free amine to be used in subsequent coupling or derivatization chemistry. Industrial relevance arises from its role as a manufacturable chiral feedstock for producing cyano-functional amino acid derivatives used in research-grade and process-scale fine chemical synthesis.
4. Side-Chain And Nitrile Functionalization
Cbz-2-Cyano-L-Phenylalanine is applicable to functional group transformation strategies that exploit the nitrile as a versatile synthetic handle. The nitrile substituent can undergo conversion routes to generate amide-containing motifs or enable cyclization chemistry to access heterocyclic frameworks derived from amino acid precursors. The N-Cbz protection allows orthogonal handling of the amino functionality, supporting selective transformations at the nitrile while preserving the protected amine until deprotection is desired. Downstream utility includes preparation of functionalized amino acid derivatives and intermediate sets used for combinatorial synthesis, medicinal chemistry library generation, and targeted scaffold diversification.
5. Chemical Biology Labeling
Cbz-2-Cyano-L-Phenylalanine can be used in chemical biology workflows that require incorporation of a defined, stable amino acid residue into labeled peptides or probes. The protected amino group enables controlled peptide coupling to introduce the cyano-bearing phenylalanine unit into biomolecule-reactive constructs, while the L-stereochemistry helps preserve recognition-dependent conformations in peptide-based probes. The nitrile functionality provides a chemically defined feature that can be retained for later derivatization or used as a non-reducing, low-reactivity handle during conjugation sequence design. Resulting labeled or derivatized peptide materials can support biochemical research intermediate preparation and analytical reagent development where stereochemical fidelity and functional group orthogonality matter.
6. Pharmaceutical Intermediate Preparation
Cbz-2-Cyano-L-Phenylalanine is suitable for pharmaceutical intermediate preparation and process chemistry development targeting cyano-containing amino acid derivatives and peptide-like intermediates. The N-Cbz carbamate offers a reproducible protecting-group strategy compatible with common peptide coupling and intermediate isolation steps, while the alpha-cyano substitution provides a functional motif that can be carried into downstream synthesis for analog generation. The aromatic phenylalanine framework supports integration into larger chiral sequences, enabling stepwise assembly of protected intermediates used in manufacturing-oriented synthetic routes. Broader relevance includes its use as a defined chiral feedstock for producing structured intermediates that can be further transformed into peptidomimetic or heterocycle-containing building blocks for specialty chemical production.
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