Cbz-2-Chloro-L-Phenylalanine is a Cbz-protected, L-phenylalanine-derived amino acid featuring a chloro substituent at the 2-position of the side-chain-bearing carbon framework and a phenyl side chain. The molecule contains an N-Cbz carbobenzyloxy protecting group on the amino functionality and a free carboxylic acid, with the stereochemistry indicated as L at the alpha carbon, while the 2-chloro substituent provides a halogenated handle that can influence reactivity and physicochemical properties during peptide assembly. As a protected amino acid building block, it is used in peptide synthesis workflows to control chemoselectivity of the amino group while the chloro-substituted phenylalanine motif supports structure-activity and labeling studies that require a halogen-bearing aromatic residue.
CAT No: CP11408
Cbz-2-Chloro-L-Phenylalanine is a Cbz-protected L-phenylalanine derivative in which the alpha position bears a chloro substituent, establishing a defined stereochemical relationship between the chiral center and the side-chain phenyl ring. The molecule contains a carbamate-protected amino group (Cbz), a carboxylic acid functionality, and an electrophilic 2-chloro substituent that can participate in nucleophilic substitution or elimination chemistry under appropriate conditions. The aromatic side chain and the benzyloxycarbonyl group provide conformational and reactivity handles that are compatible with protected amino acid synthesis workflows. As a chiral amino acid intermediate, it is commonly used to access halo-substituted phenylalanine motifs and to generate downstream derivatives for peptide coupling, side-chain functionalization, and stereocontrolled scaffold elaboration.
1. Peptide Synthesis
Cbz-2-Chloro-L-Phenylalanine supports peptide building-block preparation for solid-phase or solution-phase assembly where an N-Cbz protected amino acid is required. The Cbz carbamate enables standard peptide coupling after activation of the carboxyl group while maintaining the amino functionality in a protected state during chain elongation. The 2-chloro alpha substituent can serve as a latent functional handle for subsequent transformations after incorporation into peptide sequences or peptide fragments. Downstream deprotection and side-chain modification strategies can generate halo-containing peptide analogs suitable for studying how alpha-functionalization influences conformational properties and reactivity.
2. Chiral Amino Acid Derivatization
Cbz-2-Chloro-L-Phenylalanine is used as a chiral amino acid intermediate for stereoselective derivatization of the alpha-chloro center into substituted analogs. The combination of a protected amine (Cbz) and a carboxylic acid allows orthogonal protection management, enabling selective activation for coupling or conversion while preserving the ability to manipulate the chloro-bearing stereocenter. Nucleophilic substitution or related substitution-elimination pathways can be applied to introduce heteroatom-containing substituents that tune polarity and hydrogen-bonding patterns relative to unmodified phenylalanine. The resulting derivatives can then be carried into peptide construction, SAR studies, or fragment elaboration where stereochemical fidelity at the alpha position is required.
3. Peptidomimetic Construction
Cbz-2-Chloro-L-Phenylalanine participates in peptidomimetic and constrained scaffold synthesis where alpha-functionalized phenylalanine units are incorporated to modulate backbone behavior. The protected amino group and carboxylic acid support conversion into activated forms for coupling to amine or hydroxyl nucleophiles that build non-natural peptide-like architectures. The 2-chloro substituent can be retained as a reactive motif for further functionalization, enabling access to substituted analogs that may alter steric and electronic effects around the backbone. Downstream formation of peptide analog libraries supports chemical biology and medicinal chemistry workflows focused on mapping structural determinants of molecular recognition.
4. Chemical Biology Probes
Cbz-2-Chloro-L-Phenylalanine can be applied in chemical biology research to generate reactive amino acid motifs for probe development and labeling strategies. The alpha-chloro functionality provides a handle for installing functional groups that can later engage in covalent or affinity-based interactions with biomolecular targets under controlled conditions. The Cbz protection allows sequential synthetic steps that separate peptide-compatible handling from later probe activation or conjugation chemistry. Generated derivatives can serve as intermediates for biomolecule-modifying reagents, enabling mapping of binding environments and reactivity patterns in protein-focused studies.
5. Pharmaceutical Intermediate Preparation
Cbz-2-Chloro-L-Phenylalanine is suitable for pharmaceutical intermediate preparation in fine chemical synthesis routes that require a stereodefined, N-protected amino acid with an electrophilic alpha substituent. The Cbz carbamate supports controlled deprotection and subsequent coupling or conversion steps, while the carboxylic acid enables formation of activated intermediates used in downstream assembly. The 2-chloro group can be leveraged to introduce functional diversity during process chemistry, including incorporation of heteroatom substituents that adjust solubility, polarity, and chemical stability of advanced intermediates. The compound's structure aligns with manufacturing-oriented intermediate design for producing halo-substituted phenylalanine derivatives used in peptide-like drug candidates and related synthetic programs.
6. Process Chemistry Intermediate
Cbz-2-Chloro-L-Phenylalanine serves as a process chemistry intermediate for scalable synthesis of alpha-functionalized phenylalanine derivatives. The presence of a robust N-Cbz protecting group supports handling across multi-step sequences, including activation of the carboxyl group for coupling chemistry and later deprotection when the amino functionality must be exposed. The electrophilic chloro substituent enables conversion into a range of substituted products through nucleophile-controlled transformations, supporting route flexibility in industrial intermediate preparation. Downstream derivatives produced from this chiral amino acid intermediate can be directed into specialty chemical production and industrial manufacturing streams where stereochemically defined building blocks are required.
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