Cbz-2-Chloro-D-Phenylalanine is a protected, non-natural amino acid derivative featuring a D-phenylalanine backbone bearing a 2-chloro substituent on the alpha carbon and a benzyl carbamate (Cbz) protecting group on the amino functionality. The molecule contains a free carboxylic acid and an aniline-like aromatic side chain, with the Cbz group masking the primary amine to control chemoselectivity during peptide-coupling chemistry. In synthetic peptide and amino acid derivative workflows, it is employed as a stepwise building block to introduce the alpha-chloro, aromatic amino acid motif while enabling orthogonal handling of the protected amine and the carboxyl group for assembly and subsequent downstream transformations.
CAT No: CP11500
Cbz-2-Chloro-D-Phenylalanine is a Cbz-protected D-phenylalanine derivative featuring a stereogenic α-carbon and a 2-chloro substituent adjacent to the carboxylate-bearing backbone. The molecule combines a benzyloxycarbonyl (Cbz) carbamate on the amino function with a side-chain phenyl group and a reactive α-chloride that can participate in substitution and elimination chemistry under appropriate conditions. The D-configuration provides defined stereochemical control for downstream peptide coupling and for preparing chiral amino acid intermediates that preserve configuration during functional transformations. The presence of the α-chloro handle, together with the protected amine, makes the compound a practical intermediate for amino acid derivatization and for constructing stereochemically defined peptide analogs.
1. Peptide Synthesis
Cbz-2-Chloro-D-Phenylalanine supports peptide building workflows where a Cbz-protected amino group enables amide bond formation using standard peptide coupling strategies after orthogonal deprotection. The D-phenylalanine stereocenter and the side-chain phenyl ring are compatible with incorporation into peptide sequences as a chiral residue, while the 2-chloro substituent can be retained for later functional conversion or used as a chemically addressable site. The α-chloro functionality can be carried through protected-amino-acid handling and then transformed into alternative leaving-group or nucleophile-reactive motifs to generate peptide analogs with modified backbone reactivity. Downstream, the compound can serve as a chiral intermediate for preparing stereodefined peptide fragments and for studying how α-substitution patterns influence peptide chemistry.
2. Amino Acid Derivatization
Cbz-2-Chloro-D-Phenylalanine functions as a chiral amino acid intermediate for side-chain and backbone-adjacent derivatization where the α-chloro group acts as a handle for substitution chemistry. The protected carbamate (Cbz) helps manage amine reactivity during transformations, allowing selective reactions at the α-chloride without uncontrolled amino functionalization. The D-configuration provides stereochemical fidelity for producing enantiodefined analogs used in synthetic organic chemistry and biochemical reagent development. The resulting derivatives can be used to generate C-terminal or backbone-modified amino acid building blocks, supporting downstream construction of peptidomimetics and structure-focused analog libraries.
3. Chemical Biology Probes
Cbz-2-Chloro-D-Phenylalanine can be applied in chemical biology research requiring stereochemically defined amino acid analogs for probing peptide recognition and backbone-dependent processes. The Cbz-protected amine and the α-chloro substituent enable controlled conversion into electrophilic or functionalized backbone variants that can later be used for conjugation or labeling strategies. The aromatic phenyl side chain supports hydrophobic and π-interaction patterns often relevant to molecular recognition in peptide-like systems. The compound's defined stereochemistry makes it suitable for generating probe scaffolds where configuration at the α-carbon is a key variable in biochemical investigations.
4. Peptidomimetics And SAR
Cbz-2-Chloro-D-Phenylalanine is suitable for peptidomimetic construction and structure-activity relationship studies where backbone modification at the α-position is used to tune conformational preferences and chemical reactivity. The D-phenylalanine framework provides a stereodefined scaffold, while the 2-chloro group can be transformed into alternative substituents that modulate stability, polarity, or reactivity of the resulting analogs. The Cbz protection strategy supports sequential synthetic planning, enabling selective deprotection and coupling steps that preserve the desired stereochemical outcome. Downstream use includes preparing analog series for SAR studies in medicinal chemistry and for generating defined peptide-mimic fragments for screening and mechanistic comparisons.
5. Pharmaceutical Intermediate Preparation
Cbz-2-Chloro-D-Phenylalanine serves as a chiral intermediate for fine chemical synthesis routes that require protected amino acid derivatives with an electrophilic α-functional group. The carbamate-protected amine supports controlled handling during multi-step synthesis, while the α-chloride can participate in downstream transformations toward backbone-functionalized intermediates used in drug-discovery chemistry. The D-stereochemistry can be retained through protection, coupling, and selective conversion steps, supporting the manufacture of stereochemically consistent building blocks. The compound can be employed in process chemistry intermediate preparation where orthogonal protection and a reactive α-site enable scalable synthesis of amino acid-derived intermediates and peptide analog precursors.
6. Specialty Chemical Manufacturing
Cbz-2-Chloro-D-Phenylalanine can be utilized in specialty chemical production and industrial intermediate preparation where chiral amino acid derivatives are required for downstream functionalization and incorporation into larger molecules. The Cbz-protected amine provides a stable, isolable form for manufacturing logistics, while the 2-chloro substituent offers a defined reactive site for conversion into substituted derivatives used in polymerizable or conjugatable building blocks. The phenylalanine-derived aromatic side chain supports compatibility with aromatic-rich scaffold synthesis and can influence solubility and reactivity profiles in downstream manufacturing steps. The compound thus functions as a chiral, protected amino acid starting material for generating stereodefined intermediates used in applied chemical manufacturing and industrial fine-chemical synthesis.
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