Cbz-3-Chloro-D-Phenylalanine is a Cbz-protected, non-natural amino acid derivative featuring a benzyl carbamate (Cbz) on the amino group and a 3-chloro-substituted phenyl side chain characteristic of a halogenated phenylalanine analogue. The molecule contains both an amino acid carboxyl group and a stereodefined D-configuration at the alpha carbon, with the side chain bearing a chlorinated aromatic ring that modulates polarity and electrophilic/steric behavior relative to unsubstituted phenylalanine. As a protected amino acid intermediate, it is used in peptide synthesis workflows to control chemoselectivity at the amine while enabling incorporation of the 3-chloro phenylalanine motif into peptide structures for structure-activity studies, chemical biology probes, or analytical method development.
CAT No: CP11509
Cbz-3-Chloro-D-Phenylalanine is a D-configuration phenylalanine derivative bearing a benzyloxycarbonyl (Cbz) protecting group on the amino function and a 3-chloro substituent on the aromatic ring. The molecule combines a stereogenic alpha-carbon with an aryl chloride handle, while the Cbz carbamate provides controlled amide/peptide coupling compatibility and orthogonal deprotection behavior under hydrogenolysis conditions. The presence of both a protected amine and an aryl halide enables staged synthetic logic, where the chloro substituent can participate in cross-coupling or nucleophilic aromatic substitution after peptide assembly or during side-chain functionalization. As a chiral amino acid intermediate, it supports downstream construction of D-amino acid containing peptides, peptidomimetics, and chemically diversified aromatic scaffolds for structure-focused studies.
1. Peptide Synthesis
Cbz-3-Chloro-D-Phenylalanine is used in peptide building workflows to introduce a D-amino acid residue with a protected carbamate-form amino group compatible with standard peptide coupling chemistries. The Cbz group protects the alpha-amino functionality during chain elongation, while the 3-chloro aromatic substituent remains intact to preserve a defined side-chain topology in the growing sequence. Incorporation of the D-stereocenter can modulate backbone conformation and protease resistance patterns in peptide analogs, supporting peptide science and peptidomimetic design efforts. The aryl chloride can also serve as a later-stage diversification point for post-assembly derivatization, enabling access to chlorinated or cross-coupled analog series for SAR studies and synthetic refinement.
2. Side-Chain Functionalization
Cbz-3-Chloro-D-Phenylalanine supports side-chain functionalization strategies in synthetic organic chemistry by providing an aryl chloride substituent positioned for selective transformation without disturbing the protected amino terminus. The Cbz-protected nitrogen allows orthogonal handling, where aromatic halide chemistry can be executed while the amino functionality remains protected, reducing undesired side reactions. Conversion of the aryl chloride via cross-coupling or related substitution chemistry can generate substituted phenylalanine derivatives that retain the D-chiral backbone for stereochemically defined analog libraries. Downstream, the resulting functionalized aromatic side chains can be used to tune hydrophobicity, electronic character, and binding motifs in peptidomimetics and constrained peptide frameworks.
3. Chiral Amino Acid Intermediate
Cbz-3-Chloro-D-Phenylalanine is applied as a chiral amino acid intermediate for constructing D-amino acid containing scaffolds in fine chemical synthesis and research-grade method development. The D-configuration at the alpha-carbon provides stereochemical control for downstream peptide construction, enabling consistent incorporation into protected amino acid sequences and chiral molecular designs. The Cbz carbamate functions as a stable protecting-group platform during intermediate handling, while the aryl chloride provides a chemically addressable site for later diversification to create multiple stereochemically matched derivatives. This combination can be used to prepare defined chiral building blocks for fragment-based molecular design, SAR studies, and stereochemical probes that rely on maintaining absolute configuration through multiple synthetic steps.
4. Bioconjugation Chemistry
Cbz-3-Chloro-D-Phenylalanine can be utilized in bioconjugation-oriented chemical biology workflows where D-amino acid residues and aromatic handles contribute to conjugate stability and controlled labeling chemistry. The protected amino group enables peptide or linker assembly prior to conjugation, while the 3-chloro aromatic moiety can serve as a latent functional handle for subsequent derivatization into coupling-ready aromatic substituents. Post-assembly modification can generate conjugation-compatible aryl derivatives that maintain the D-backbone stereochemistry, which may be relevant for constructing stable biomolecule conjugates and analytical standards. The resulting conjugation-ready amino acid or peptide fragment can then be incorporated into biomolecule labeling schemes that require defined stereochemistry and chemically stable aromatic functionality.
5. Pharmaceutical Intermediate Preparation
Cbz-3-Chloro-D-Phenylalanine is suitable for pharmaceutical intermediate preparation in process chemistry contexts where protected chiral amino acid derivatives are required for controlled synthesis of peptide-like active ingredient motifs. The Cbz-protected amine supports manufacturing-compatible peptide coupling sequences, while the aryl chloride enables divergence into substituted analogs through halide-based transformation routes. The D-stereocenter provides a consistent chiral element for generating stereochemically defined intermediates used in medicinal chemistry campaigns and process development for peptidomimetic candidates. Downstream, the compound can be converted into protected or partially deprotected intermediates that feed into larger synthetic assemblies, including analog series generation and impurity-mapped intermediate preparation for robust synthetic planning.
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