Cbz-3-Chloro-L-Phenylalanin is a Cbz-protected, α-amino acid derivative in which the phenylalanine side chain bears a 3-chloro substituent on the aromatic ring, providing a chlorinated, nonpolar aryl functionality for incorporation into peptide frameworks. The molecule contains a free carboxyl group and an N-terminus masked as a benzyloxycarbonyl (Cbz) carbamate, with the stereochemistry indicated as L at the α-carbon and the amino group therefore rendered non-nucleophilic under conditions used for peptide coupling. In peptide synthesis workflows, the Cbz protection supports stepwise chemoselective amide bond formation while the chloro-substituted aromatic side chain can be used for structure-activity studies, chemical labeling handles, or the preparation of chlorinated peptide analogues.
CAT No: CP11508
Cbz-3-Chloro-L-Phenylalanin is a Cbz-protected L-phenylalanine derivative bearing a stereogenic alpha carbon and a 3-chloro substituent on the aromatic ring. The molecule contains a carbobenzyloxy (Cbz) group on the amino functionality and a free carboxylic acid (or acid-form equivalent depending on supplier specification), combining an activated peptide-coupling handle with an aryl chloride that can participate in cross-coupling or nucleophilic aromatic substitution chemistry. The presence of the ortho/ meta relationship of the chloro substituent relative to the side-chain linkage provides a defined electronic and steric environment for downstream functionalization while preserving the L-configuration required for stereochemically consistent peptide and peptidomimetic construction. The aromatic chloride and protected amine together make the compound a chiral intermediate suitable for iterative amino acid derivatization and peptide building-block preparation.
1. Protected Amino Acid Chemistry
Cbz-3-Chloro-L-Phenylalanin is used in protected amino acid synthesis workflows where the Cbz carbamate stabilizes the amino group during acid activation and coupling steps. The L-configuration at the alpha carbon supports stereochemically controlled peptide bond formation, while the carboxylic acid functionality enables conversion to activated esters or direct coupling to amines under standard peptide chemistry conditions. The aryl chloride on the side-chain ring remains chemically addressable after protection, allowing orthogonal downstream transformations without disturbing the peptide-compatible functional groups. The resulting derivatives can be carried forward into sequential protection/deprotection strategies and used as intermediates for generating libraries of chlorinated phenylalanine analogs.
2. Peptide Synthesis
Cbz-3-Chloro-L-Phenylalanin serves as a peptide building block for incorporating a chlorinated aromatic side chain into linear peptides and protected peptide fragments. The Cbz-protected amine supports selective coupling at the alpha-carboxyl group, while the intact aromatic chloride can be retained through peptide assembly and later transformed to diversify side-chain functionality. L-stereochemistry is maintained through the building-block stage, supporting consistent conformational and recognition properties in peptide analogs where side-chain electronics and sterics are tuned by the 3-chloro substituent. The compound can be applied to the preparation of peptide substrates, peptide inhibitors, and peptidomimetic precursors that require a defined chloroaryl motif for subsequent functionalization.
3. Side-Chain Functionalization
Cbz-3-Chloro-L-Phenylalanin is suitable for side-chain functionalization strategies that exploit the aryl chloride as a reactive handle for C-C and C-heteroatom bond formation. The chlorinated phenyl ring can be converted into substituted aryl systems through cross-coupling or nucleophilic aromatic substitution approaches, enabling installation of pharmacophore-like substituents while the Cbz group can be removed or retained depending on the synthetic sequence. The protected amino acid framework supports chemoselective manipulation, since the carbamate protection can prevent unwanted amine reactivity during side-chain derivatization. Downstream products include chlorinated-to-substituted phenylalanine derivatives and peptide analogs bearing tailored aromatic substituents for structure-function studies.
4. Drug Discovery Intermediates
Cbz-3-Chloro-L-Phenylalanin is applied as a chiral intermediate in medicinal chemistry programs that require incorporation of halogenated amino acid motifs into lead scaffolds. The combination of a stereogenic amino acid backbone and a 3-chloroaryl side chain supports fragment-based and SAR-oriented synthesis of analog series where electronic effects and steric profiles are modulated by aromatic substitution. The Cbz-protected amine and carboxylic acid enable conversion into coupling-ready forms for assembling constrained peptidomimetics, while the aryl chloride provides a late-stage diversification point for generating multiple analogs from a common chiral precursor. The compound thereby functions as a practical upstream feedstock for fine chemical synthesis of amino acid-derived molecular entities used in discovery workflows.
5. Process Chemistry Intermediate
Cbz-3-Chloro-L-Phenylalanin is relevant to process chemistry and specialty chemical production as a stable, isolable chiral amino acid derivative that can be handled as a protected building block. The Cbz carbamate offers a protection strategy compatible with common coupling and intermediate purification steps, while the aryl chloride provides a defined functional group for downstream conversion into substituted intermediates without requiring complete re-synthesis of the amino acid core. The preserved L-stereochemistry supports manufacturing routes that avoid racemization-prone transformations after the chiral center is established. The compound can be employed to prepare chlorinated phenylalanine derivatives and peptide-grade intermediates for scale-up-oriented synthesis of amino acid-based products.
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