Cbz-3,5-Dichloro-L-Phenylalanine is a protected amino acid derivative in which the phenylalanine scaffold bears two chlorine substituents at the 3- and 5-positions of the aromatic ring, and the amino group is protected as a benzyloxycarbonyl (Cbz, Z) carbamate. The molecule contains a free carboxylic acid functional group and an anilide-like aromatic side chain with increased halogen substitution, while the stereochemistry is specified as L for the α-carbon. As a Cbz-protected, halogenated phenylalanine building block, it is used in peptide synthesis and structure-activity or binding studies where controlled incorporation of a dichloro-substituted aromatic side chain helps probe effects of sterics and electronics, and the Cbz group supports chemoselective stepwise assembly of peptide intermediates.
CAT No: CP12508
Cbz-3,5-Dichloro-L-Phenylalanine is an L-phenylalanine derivative bearing a benzyloxycarbonyl (Cbz) N-protecting group and two chlorine substituents at the 3 and 5 positions of the aromatic ring. The molecule retains the stereogenic center of the L-amino acid backbone, with the side-chain carboxyl functionality protected as a free acid or as an amino-acid building block depending on the supplier specification, while the Cbz carbamate provides stable handling under peptide-coupling conditions. The 3,5-dichloro substitution increases aromatic electron-withdrawing character and modulates hydrophobicity and steric profile, which can influence coupling reactivity and downstream derivatization of the side-chain aryl ring. The presence of a removable Cbz group and a functional amino-acid framework makes the compound suitable for peptide building block preparation, chiral intermediate use, and aromatic functional transformation in synthetic organic chemistry.
1. Peptide Synthesis
Cbz-3,5-Dichloro-L-Phenylalanine is applied in peptide synthesis workflows where an N-Cbz protected amino acid with a defined L-configuration is required for controlled amide bond formation. The Cbz carbamate protects the amino functionality during coupling, while the amino acid backbone provides the nucleophilic amine equivalent after deprotection planning and the carboxyl group participates as the coupling handle. The 3,5-dichloro phenyl side chain can be incorporated as a sterically demanding, electronically tuned residue that helps define aromatic spacing and hydrophobic character in peptide sequences. The resulting peptide analogs can serve as research-grade substrates for structure-activity relationship studies, sequence optimization, and method development in protected amino acid chemistry.
2. Peptidomimetics And SAR
Cbz-3,5-Dichloro-L-Phenylalanine supports peptidomimetic and SAR-focused synthesis by enabling incorporation of a halogenated aromatic pharmacophore into constrained peptide-like scaffolds. The L-phenylalanine stereocenter provides stereochemical control that can be carried into downstream cyclizations, conformational restriction strategies, or side-chain functional elaboration. The dichloro substitution pattern at the 3 and 5 positions can be leveraged for later aromatic transformations, including selective cross-coupling or ring-functionalization steps that preserve the amino acid-derived stereochemical information. The compound thereby functions as a chiral aromatic residue source for generating libraries of analogs used in SAR studies and fragment-based molecular design.
3. Side-Chain Functionalization
Cbz-3,5-Dichloro-L-Phenylalanine is suitable for synthetic routes that require aryl-halide chemistry after N-protection management, because the 3,5-dichloro pattern provides handles for chemoselective substitution. The protected amino acid framework allows orthogonal manipulation: Cbz can be retained during early stages of aryl functionalization planning and removed later to enable peptide coupling or conjugation. The dichloro aromatic ring can undergo nucleophilic aromatic substitution or transition-metal-catalyzed cross-coupling to introduce heteroaryl groups, alkyl substituents, or solubilizing motifs while maintaining the amino acid backbone as a chiral scaffold. The resulting functionalized derivatives can be used to prepare downstream intermediates for medicinal chemistry, chemical biology probes, and industrial fine-chemical targets requiring halogenated aromatic substitution patterns.
4. Chemical Biology Probes
Cbz-3,5-Dichloro-L-Phenylalanine can be employed in chemical biology research where halogenated aromatic amino acid residues are incorporated into labeling reagents or affinity-tagged peptide constructs. The Cbz-protected amine enables stepwise assembly of peptide conjugates, while the L-configuration supports stereochemically defined recognition in receptor- or enzyme-binding contexts. The electron-withdrawing dichloro aromatic ring can influence binding interactions and can serve as a stable motif in probe scaffolds that require consistent hydrophobic and steric properties. The protected amino acid derivative can therefore be used as a building block for biomolecule modification strategies, including preparation of probe libraries and analytical standards derived from defined peptide sequences.
5. Pharmaceutical Manufacturing Intermediates
Cbz-3,5-Dichloro-L-Phenylalanine is relevant to pharmaceutical manufacturing and process chemistry as a protected amino acid intermediate for producing halogenated aromatic peptide fragments used in active ingredient synthesis. The Cbz protecting group supports robust handling during coupling and purification operations, and its planned deprotection provides a predictable switch from protected building block to coupling-ready amino functionality. The halogenated phenyl side chain can be carried through manufacturing steps to maintain a defined aromatic substitution pattern that may be required in final drug substance or drug-substance-related intermediates. The compound's structure aligns with industrial protected amino acid synthesis logic, enabling controlled assembly of stereodefined residues and supporting downstream conversion into peptide-derived intermediates suitable for fine chemical production.
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