Cbz-3,5-Dichloro-D-Phenylalanine is a protected, non-natural amino acid derivative in which D-phenylalanine bears two chloro substituents at the 3 and 5 positions of the aromatic side chain. The molecule contains a free carboxyl group and an amino group masked as a Cbz (benzyloxycarbonyl) carbamate, while the chlorinated phenyl ring provides increased hydrophobicity and electron-withdrawing character compared with unsubstituted phenylalanine. In peptide chemistry, this Cbz-protected amino acid is used as a building block for preparing modified peptides or peptide analogues via stepwise coupling, and the halogenated aromatic side chain can serve as a handle for structure-activity studies, labeling strategies, or analytical method development.
CAT No: CP12509
Cbz-3,5-Dichloro-D-Phenylalanine is a Cbz-protected D-phenylalanine derivative bearing two chlorine atoms on the 3,5-positions of the aromatic ring, creating a sterically and electronically differentiated side chain. The molecule contains a benzyloxycarbonyl (Cbz) carbamate on the amino group and a free carboxylic acid functionality typical of amino acid building blocks, enabling controlled peptide coupling and protecting-group management. The D stereocenter at the alpha carbon supports stereochemically defined incorporation into peptide sequences and chiral synthetic routes, while the dichlorinated aryl ring can participate in electrophilic aromatic substitution conditions and can influence hydrophobicity and conformational preferences in downstream amides. The presence of an acid and a protected amine makes it suitable as a chiral intermediate for protected amino acid synthesis, peptide building block preparation, and derivatization workflows that rely on orthogonal reactivity.
1. Peptide Synthesis
Cbz-3,5-Dichloro-D-Phenylalanine is used in peptide synthesis workflows where a Cbz-protected amino acid provides a stable N-protection handle during coupling chemistry. The Cbz carbamate and the carboxylic acid group enable standard amide bond formation strategies while maintaining the D-configuration at the alpha carbon for stereodefined peptide construction. The 3,5-dichloro substituted phenyl side chain can be incorporated to tune aromatic bulk and halogen-driven interactions in peptide backbones and side-chain modified analogs. Downstream deprotection of the Cbz group can regenerate the free amine for sequential chain elongation, supporting multi-step protected amino acid chemistry and peptide building block preparation.
2. Peptidomimetics And SAR Studies
Cbz-3,5-Dichloro-D-Phenylalanine is applied in peptidomimetic design and structure-activity relationship studies where halogenated aromatic residues are used to modulate binding-site complementarity and metabolic stability proxies. The dichlorinated phenyl ring, combined with the D-amino acid stereochemistry, can be incorporated into peptide analog scaffolds to create defined conformational and electronic effects around the amide linkage. The protected amino acid format supports iterative synthesis of analog libraries using consistent coupling and deprotection cycles, including workflows that require orthogonal handling of the N-protecting group. The resulting halogenated amide products can serve as SAR intermediates for downstream functionalization, scaffold diversification, and comparative analytical evaluation.
3. Chemical Biology Probes
Cbz-3,5-Dichloro-D-Phenylalanine is suitable for chemical biology research that requires incorporation of a stereochemically defined, halogenated aromatic residue into peptide-based probes. The Cbz-protected amine and carboxylic acid enable attachment to linker-bearing fragments or capture handles through amide formation, supporting probe construction for target engagement studies at the molecular level. The 3,5-dichlorophenyl side chain can function as a hydrophobic and electronically biased motif that may influence probe partitioning and binding orientation within biochemical assays. The D-configuration provides a means to control stereochemical presentation in receptor-binding motifs and to generate stereoisomeric probe sets for mechanistic and specificity investigations.
4. Protected Amino Acid Chemistry
Cbz-3,5-Dichloro-D-Phenylalanine is employed as a chiral intermediate in protected amino acid synthesis, where the Cbz group provides a robust N-protection strategy compatible with peptide coupling conditions. The amino acid architecture, featuring an N-protected carbamate and a carboxylic acid, supports orthogonal transformations that separate N-deprotection from side-chain or aromatic functional modifications. The dichlorinated aromatic ring can withstand many standard peptide-manufacturing conditions, allowing the compound to be carried through multi-step sequences that generate protected amino acid derivatives and sequential coupling partners. The compound can also be used to prepare downstream derivatives such as activated esters, coupling reagents, or further protected forms that maintain D stereochemical integrity.
5. Pharmaceutical Intermediate Preparation
Cbz-3,5-Dichloro-D-Phenylalanine is relevant to pharmaceutical intermediate preparation and fine chemical synthesis where halogenated amino acid residues are incorporated into peptide-like intermediates and small-molecule fragments. The Cbz-protected D-phenylalanine framework supports controlled assembly of amide-containing intermediates that can be carried into later stages of medicinal chemistry without losing stereochemical definition. The 3,5-dichlorophenyl group can serve as a chemically stable aromatic handle that influences physicochemical properties of intermediates and can be used to construct analog series with systematic electronic variation. The compound's protected amino acid format aligns with industrially practical intermediate strategies that rely on predictable deprotection and coupling compatibility in manufacturing routes for chiral building blocks.
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