Cbz-4-Chloro-L-Phenylalanine is a Cbz-protected, L-phenylalanine-derived amino acid derivative in which the aromatic side chain bears a 4-chloro substituent, classifying it as a substituted phenylalanine analogue for peptide chemistry. The molecule contains a free carboxyl group and an N-terminus protected as a benzyloxycarbonyl (Cbz) carbamate, with the side chain featuring a chlorinated benzyl aromatic functionality while the stereocenter is specified as L. In synthesis, it is employed as a protected amino acid building block for stepwise peptide assembly and for preparing peptide analogues that incorporate a para-chloro aromatic side chain for structure-activity, binding, or chemical labeling studies.
CAT No: CP11608
Cbz-4-Chloro-L-Phenylalanine is an N-Cbz-protected L-phenylalanine derivative bearing a para-chloro substituent on the aromatic ring, providing a chiral amino acid framework with an electron-withdrawing aryl halide handle. The molecule contains a carbamate-protected primary amine (Cbz), a free carboxylic acid functionality or acid-form equivalent depending on supplier specification, and a stereogenic center at the α-carbon consistent with L-configuration. The para-chloro substituent modulates aromatic reactivity and can participate in downstream cross-coupling or nucleophilic aromatic substitution chemistry after selective functional group manipulation. The Cbz group enables controlled peptide coupling workflows through standard deprotection strategies while preserving the stereochemical integrity of the amino acid during synthesis and intermediate preparation.
1. Peptide Synthesis
Cbz-4-Chloro-L-Phenylalanine is used as a protected amino acid building block for assembling peptide chains in solution-phase and solid-phase peptide synthesis. The Cbz-protected amine supports reliable amide bond formation at the nitrogen while the L-configuration at the α-carbon provides stereochemical fidelity during coupling. The para-chloro phenyl side chain can be retained through peptide assembly and later transformed to diversify peptide analogs via aryl functionalization. The resulting chloro-substituted peptide products serve as defined scaffolds for studying how aromatic halide substitution influences conformational preferences and molecular recognition in peptide science and SAR investigations.
2. Side-Chain Functionalization
Cbz-4-Chloro-L-Phenylalanine is applied in synthetic organic chemistry and chemical biology workflows that require late-stage diversification of an amino acid side chain. The para-chloro substituent functions as a synthetic handle for cross-coupling reactions or related aryl substitution strategies after Cbz removal and/or orthogonal protection adjustments. The carbamate protection strategy allows the amino acid to be carried through peptide coupling or intermediate derivatization while minimizing undesired amine reactivity. Downstream conversion of the aryl chloride enables access to substituted phenylalanine analogs that can be incorporated into peptidomimetics, linker-bearing constructs, or chemically defined probes for structure-function studies.
3. Drug Discovery Scaffolds
Cbz-4-Chloro-L-Phenylalanine is utilized in medicinal chemistry research for constructing chiral, aromatic-rich fragments and peptidomimetic motifs used in structure-activity relationship studies. The combination of an L-phenylalanine backbone with a para-chloro aryl group supports systematic exploration of electronic and steric effects on binding-site interactions in designed analog series. The Cbz-protected amine provides a controlled entry point for preparing N-linked intermediates, including amide and peptide-like linkages common in fragment elaboration. The chloroaryl functionality can be further elaborated into diverse substituent patterns to generate analog libraries that support SAR mapping and molecular design iterations.
4. Protected Amino Acid Chemistry
Cbz-4-Chloro-L-Phenylalanine is suitable for protected amino acid synthesis and intermediate preparation where orthogonal protection and stereochemical control are required. The Cbz carbamate protects the α-amino group during carboxyl activation and coupling chemistry, enabling selective transformations at the carboxyl side without compromising the amino stereocenter. The aryl chloride remains a stable substituent under many peptide coupling conditions, allowing the compound to serve as a chiral intermediate for subsequent functional group interconversions. The material can be employed to produce N-deprotected amino acid derivatives, activated carboxylic acid intermediates, or protected derivatives that feed into downstream peptide building block preparation and fine chemical synthesis.
5. Pharmaceutical Manufacturing Intermediates
Cbz-4-Chloro-L-Phenylalanine is relevant to pharmaceutical manufacturing and specialty chemical production as a defined chiral intermediate for producing chloro-substituted amino acid residues used in peptide-like active ingredient candidates and process development. The Cbz-protected amine aligns with scalable peptide coupling strategies that require predictable protection behavior and controlled deprotection steps to expose the free amino group when needed. The para-chloro aromatic group provides a stable, process-compatible handle for subsequent synthetic elaboration toward substituted aryl variants during route design. The compound's structure supports its use in controlled intermediate sequences that generate consistent stereochemical outcomes and enable manufacturing of chemically characterized amino acid-derived intermediates for downstream formulation and analytical qualification workflows.
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