D-4-Chlorophenylglycine is a D-configured, non-proteinogenic amino acid derivative featuring a glycine backbone substituted at the alpha carbon with a 4-chlorophenyl group, classifying it as an aryl-substituted amino acid. The molecule contains a primary amino group and a carboxylic acid functional group, with the side chain bearing a para-chloro substituent on the aromatic ring that can modulate hydrophobicity and electronic character while maintaining the D stereocenter. D-4-Chlorophenylglycine is used in peptide and peptidomimetic synthesis and chemical biology studies as a stereodefined building block for incorporating an aryl-bearing, halogenated residue into structure-activity and labeling workflows.
CAT No: CP10103
D-4-Chlorophenylglycine is a D-configured amino acid featuring a benzylic side chain bearing a para-chloro substituent on the aromatic ring, coupled to a stereogenic center at the glycine alpha carbon. The molecule contains a primary amine and a carboxylic acid in its native form, enabling standard amino acid coupling chemistry while the aryl chloride provides a chemically stable handle for later derivatization. The D-configuration supports stereochemically defined incorporation into chiral peptide-like frameworks and other asymmetric syntheses where enantiopurity matters. The combination of an aromatic ring, a reactive amine/carboxyl pair, and a para-chloro electrophile makes D-4-Chlorophenylglycine a practical intermediate for downstream construction of substituted aromatic amino acid derivatives and chiral intermediates.
1. Peptide Coupling Building Blocks
D-4-Chlorophenylglycine is used in peptide synthesis workflows where a D-amino acid residue is required to introduce stereochemical control and modulate conformational preferences in peptide backbones. The amino acid's carboxyl group can be activated for amide bond formation, while the primary amine participates in N-protection strategies such as Boc, Cbz, or Fmoc to enable orthogonal coupling sequences. The para-chloro substituted phenyl side chain can tolerate common peptide coupling conditions and can serve as a later functionalization site via nucleophilic aromatic substitution or cross-coupling after peptide assembly. The resulting D-aryl glycine-containing peptides and peptidomimetics are relevant as research-grade building blocks for scaffold diversification and structure-activity relationship studies in medicinal chemistry programs.
2. Chiral Intermediate For SAR Studies
D-4-Chlorophenylglycine is applied as a chiral amino acid intermediate for synthetic routes that require a defined D-configuration to probe stereochemical effects on molecular recognition. The benzylic stereocenter and the electron-withdrawing para-chloro substituent on the aromatic ring support systematic derivatization of side-chain electronics and steric presentation. The amine and carboxylic acid enable conversion into protected derivatives and activated esters or acid chlorides, supporting rapid generation of analog libraries for SAR studies. Downstream products can include D-aryl glycine substituted fragments, constrained peptidomimetics, and chiral heteroatom-linked derivatives used to map structure-function relationships in applied organic synthesis.
3. Side-Chain Functionalization Chemistry
D-4-Chlorophenylglycine is suitable for side-chain functionalization strategies that leverage the aryl chloride as a synthetic handle while preserving the amino acid framework for further coupling. The para-chloro group can be transformed into aryl ethers, thioethers, amines, or other substituted motifs through nucleophilic aromatic substitution or transition-metal-catalyzed cross-coupling, enabling targeted tuning of polarity and binding interactions. The amino and carboxyl functionalities can be selectively protected to control chemoselectivity, allowing sequential modification of the aromatic chloride before or after peptide-compatible protection/deprotection steps. The resulting substituted D-phenylglycine derivatives can be used to generate diversified intermediates for fine chemical synthesis, chiral building block preparation, and iterative medicinal chemistry chemistry planning.
4. Unnatural Amino Acid Incorporation
D-4-Chlorophenylglycine is employed in chemical biology and peptide science as an unnatural amino acid that can be incorporated into peptides to influence stability, protease resistance, and conformational behavior. The D-configuration at the alpha carbon enables stereochemically defined incorporation when coupled under standard peptide coupling conditions using protected forms of the amino acid. The aromatic side chain bearing a para-chloro substituent can participate in hydrophobic and halogen-bonding interactions, while the chloride provides a latent functional group for post-incorporation modification. The compound thus supports the construction of D-amino acid-containing peptide analogs and peptidomimetics used to study biomolecular interactions and to generate chemically tractable scaffolds for downstream derivatization.
5. Pharmaceutical Intermediate Preparation
D-4-Chlorophenylglycine is relevant to pharmaceutical intermediate preparation where chiral amino acid derivatives serve as feedstocks for drug-like scaffold assembly. The presence of both an amine and a carboxylic acid supports transformation into protected amino acid derivatives and activated intermediates compatible with stepwise synthesis toward amide-rich structures. The para-chloro aromatic motif can be carried through multi-step sequences as a stable substituent or converted into alternative substitution patterns to adjust physicochemical properties and synthetic handles. The compound can therefore be used to manufacture process chemistry intermediates and fine chemical building blocks that feed into broader synthetic programs requiring stereochemically defined aromatic amino acid units.
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