D-4-Methoxyphenylglycine is a D-configured non-proteinogenic amino acid featuring a glycine backbone substituted with a 4-methoxyphenyl side chain, making it a substituted phenylglycine derivative. The molecule contains a free amino group and a carboxyl group alongside an ether-functional methoxy substituent on the aromatic ring, and its stereochemistry is specified as the D form. In peptide and structure-activity study contexts, this amino acid is used as a building block to introduce an aromatic, electronically modulated side chain into peptide analogues and to support chemical biology labeling or SAR investigations where phenylglycine-like residues are incorporated.
CAT No: CP10403
D-4-Methoxyphenylglycine is a chiral phenylglycine derivative in which the amino acid backbone bears a stereogenic center at the alpha carbon, and the aromatic ring carries a para-methoxy substituent that modulates electronic density and hydrogen-bonding behavior. The molecule contains a primary amino group and a carboxylic acid (or corresponding acid functionality depending on the supplied form), enabling standard amino acid coupling chemistry and salt formation, while the anisole-type methoxy group can participate as a weak hydrogen-bond acceptor and can undergo electrophilic aromatic substitution or oxidative demethylation under appropriate conditions. The para-methoxy substitution also influences conformational preferences in peptide-like scaffolds and can affect downstream transformations such as aromatic functionalization and heterocycle construction. As a D-configured chiral building block, D-4-Methoxyphenylglycine serves as a stereodefined intermediate for stereoselective synthesis, peptide analog preparation, and chiral auxiliary or fragment assembly strategies.
1. Peptide Synthesis
D-4-Methoxyphenylglycine is applied in peptide synthesis and peptide analog construction where its alpha-amino acid functionality supports amide bond formation at the backbone position. The D-configuration provides stereochemical control that can be carried through peptide coupling to generate D-amino acid residues within linear peptides, cyclic peptides, or constrained peptidomimetics. The para-methoxy aromatic side chain can be retained as a stable substituent during protected amino acid chemistry, supporting orthogonal functionalization strategies when additional reactive handles are introduced elsewhere in the sequence. Downstream peptide derivatives can be used as biochemical research tools or as chemical scaffolds for structure-activity relationship studies that probe how aromatic electronics and stereochemistry influence binding and conformational behavior.
2. Chiral Building Block Development
D-4-Methoxyphenylglycine functions as a chiral amino acid intermediate for stereoselective synthesis and chiral pool-inspired fragment assembly in fine chemical and process chemistry. The stereogenic center adjacent to the amino and carboxyl groups enables predictable stereochemical outcomes during derivatization, including conversion to protected amino acid derivatives, esterification for solubility control, and formation of activated carboxylic acid intermediates for coupling. The 4-methoxyphenyl motif can be leveraged for subsequent aromatic transformations, such as demethylation to a phenol or further electrophilic substitutions, allowing stepwise tuning of polarity and binding interactions in downstream molecules. The D-stereochemistry is particularly relevant for generating D-configured chiral centers in drug-like scaffolds and peptidomimetic frameworks where stereochemical identity must be preserved through multi-step synthesis.
3. Side-Chain Functionalization
D-4-Methoxyphenylglycine is suitable for side-chain functionalization workflows that start from an anisole-bearing aromatic ring and proceed to phenolic or substituted aromatic derivatives. The methoxy group provides a handle for controlled oxidative demethylation to yield a phenol, enabling subsequent derivatization such as ether formation, esterification, or participation in coupling reactions that require phenolic oxygen. The primary amino and carboxylic acid functionalities can be protected or converted to N- and C-terminal equivalents to allow selective chemistry on the aromatic ring without disrupting the amino acid backbone. Resulting functionalized amino acid derivatives can feed into combinatorial synthesis, SAR-focused library generation, and biomolecule labeling strategies where aromatic oxygenation patterns and stereochemistry jointly influence molecular recognition.
4. Peptidomimetics And SAR Studies
D-4-Methoxyphenylglycine is used in peptidomimetic construction and medicinal chemistry research aimed at mapping structure-activity relationships for peptide-like binding motifs. The phenylglycine backbone contributes conformational and steric features distinct from aliphatic amino acids, while the para-methoxy substituent modulates aromatic electronics and can influence intramolecular interactions in constrained analogs. D-configuration supports incorporation of stereochemically defined residues that can alter binding orientation, proteolytic stability, and overall scaffold geometry in peptide-mimicking systems. Downstream analogs derived from this amino acid can be incorporated into larger synthetic sequences to generate structure-defined libraries for SAR studies and molecular design campaigns that evaluate how aromatic substitution and stereochemistry affect target interaction patterns.
5. Pharmaceutical Intermediate Preparation
D-4-Methoxyphenylglycine serves as a pharmaceutical intermediate for manufacturing routes that require a stereodefined amino acid building block with an aromatic side chain. The amino acid functional group set supports conversion into N-protected derivatives and activated carboxylic acid forms compatible with standard peptide coupling chemistries used in fine chemical synthesis. The para-methoxyphenyl motif can be carried through intermediate stages to maintain a defined aromatic substitution pattern before later functional group interconversions, including phenol generation or further aromatic elaboration, depending on the target scaffold. Industrially, the compound's chiral center and protected-amino-acid compatibility make it suitable for process chemistry intermediate preparation where stereochemical integrity and downstream coupling readiness are required for consistent batch-to-batch synthesis of peptide-like and aromatic-containing intermediates.
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