L-4-Chlorophenylglycine is a free, naturally occurring amino acid derivative in the phenylglycine family, featuring a glycine backbone bearing a 4-chlorophenyl substituent on the side chain. The molecule contains both an amino group and a carboxyl group, and its side chain presents a para-chloro-substituted aromatic ring that can influence hydrophobicity and electronic properties relative to unsubstituted phenylglycine, with the "L" designation indicating the specified stereochemical form at the amino acid center. As a non-proteinogenic aromatic amino acid analog, it is used in peptide and structure-activity studies and can be incorporated into synthetic peptide sequences to probe the effects of aryl halogen substitution on conformation, binding interactions, or physicochemical behavior.
CAT No: CP10102
L-4-Chlorophenylglycine is an L-configured amino acid derivative featuring a glycine backbone bearing a para-chlorinated phenyl side chain, which introduces a stereochemically defined chiral center at the alpha carbon and a strongly electron-withdrawing aromatic substituent. The molecule contains a primary amino group and a carboxylic acid functionality, enabling standard amino acid coupling chemistry while also supporting selective derivatization of the side-chain aryl ring for downstream synthetic diversification. The aryl chloride can participate in cross-coupling or nucleophilic aromatic substitution strategies under appropriate conditions, while the amino and carboxyl groups can be protected or activated to control chemoselectivity during peptide construction or medicinal chemistry assembly. As a chiral aromatic amino acid intermediate, L-4-Chlorophenylglycine can be routed into protected amino acid derivatives, aryl-functionalized analogs, and conformationally informative peptidomimetic fragments.
1. Peptide Synthesis
L-4-Chlorophenylglycine is applied in peptide synthesis and peptide fragment assembly where the L-amino acid stereocenter and glycine-like backbone facilitate incorporation into dipeptides and longer sequences. The carboxylic acid and amino group can be converted into coupling-ready forms through N-protection and C-terminal activation, supporting amide bond formation with standard peptide coupling reagents while maintaining stereochemical integrity. The para-chloro substituent on the phenyl side chain can remain intact during peptide coupling and later serve as a handle for cross-coupling to generate aryl-substituted peptide analogs. The resulting chlorinated peptide building blocks are useful for library synthesis, structure-activity relationship studies, and scaffold diversification in peptide chemistry.
2. Chiral Building Blocks
L-4-Chlorophenylglycine is used as a chiral amino acid intermediate for stereoselective synthesis of aromatic, chiral fragments in fine chemical and medicinal chemistry workflows. The defined L-configuration at the alpha carbon supports predictable stereochemical outcomes when the amino acid is transformed into protected derivatives such as N-protected amino acid esters or acids. The aromatic chloride enables staged functional group interconversions, allowing the synthesis route to separate stereocenter installation from later aryl diversification. Downstream targets can include chiral peptidomimetics, constrained aromatic amino acid analogs, and intermediates bearing orthogonal functional handles suitable for sequential functional group chemistry.
3. Peptidomimetics And SAR
L-4-Chlorophenylglycine is suitable for peptidomimetic construction and structure-activity relationship (SAR) studies where the chlorinated phenyl side chain provides steric and electronic features distinct from unsubstituted phenylglycine. The amino acid core can be incorporated into amide-linked analogs, and the aryl chloride can be retained to tune binding-site interactions through subsequent aryl substitution patterns. The ability to generate a series of para-functionalized derivatives via cross-coupling supports SAR mapping while preserving the chiral backbone geometry. The compound thus functions as a practical chiral aromatic amino acid scaffold for medicinal chemistry campaigns focused on optimizing molecular recognition.
4. Side-Chain Functionalization
L-4-Chlorophenylglycine is applied in side-chain functionalization strategies that leverage the para-chloro aryl group as a synthetic handle. The aryl chloride can undergo palladium-catalyzed cross-coupling or related transformations to install substituents such as heteroaryl or alkyl groups while the amino acid functionality is protected or converted to a derivative compatible with the coupling conditions. The amino acid-derived intermediates can then be deprotected and reactivated for further coupling, enabling iterative build-up of complex chiral molecules. This approach supports the preparation of diversified chiral aromatic amino acid derivatives used in chemical biology probes, SAR libraries, and downstream synthetic intermediates.
5. Pharmaceutical Intermediate Preparation
L-4-Chlorophenylglycine is utilized as a chiral pharmaceutical intermediate in synthetic routes that require an L-configured aromatic amino acid unit. The presence of both an amino functionality and a carboxylic acid enables conversion into N-protected forms and activated C-terminal derivatives that can be incorporated into drug-like scaffolds through amide formation. The para-chloro substituent provides a chemically stable motif during intermediate handling and can be transformed later to access substituted analogs without reworking the chiral center. The compound's structure therefore supports process-oriented intermediate design for fine chemical synthesis, including the preparation of chiral building blocks used to assemble larger molecules.
6. Chemical Biology Probes
L-4-Chlorophenylglycine is suitable for chemical biology research where chiral aromatic amino acid fragments are incorporated into labeled or functionalized biomolecule-interacting constructs. The amino acid core can be protected and coupled into peptide-like structures or conjugation-ready intermediates, while the aryl chloride can serve as a latent functional handle for further derivatization toward probe generation. The stereochemical definition at the alpha carbon helps maintain consistent three-dimensional presentation of the aromatic side chain in binding studies and probe libraries. The resulting chlorinated chiral constructs can be used to support target engagement mapping, molecular recognition experiments, and analytical method development in applied biochemical research.
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