DL-4-Methoxyphenylglycine is a non-proteinogenic, aromatic amino acid derivative featuring a glycine backbone substituted with a 4-methoxyphenyl side chain, existing as a racemic mixture (DL) of stereoisomers. The molecule contains a free amino group and a carboxyl group alongside an aryl methoxy substituent, and its side chain bears a planar aromatic ring with an ether functionality that can participate in hydrogen-bonding and aromatic interactions during peptide assembly or binding studies. As an amino acid building block, it is used in peptide synthesis and structure-activity or chemical biology investigations where incorporation of a methoxy-substituted aryl glycine analogue is used to probe conformational effects, side-chain electronics, and intermolecular recognition.
CAT No: CP10401
DL-4-Methoxyphenylglycine is a racemic phenylglycine derivative in which the amino acid backbone is attached to a 4-methoxy substituted phenyl ring, providing an aromatic side chain with an electron-donating methoxy group. The molecule contains the amino and carboxylic acid functionality (or corresponding derivative forms during synthesis), enabling formation of amide and peptide bonds while supporting standard amino acid protection and coupling chemistry. The aromatic ring can participate in electrophilic aromatic substitution and oxidative or reductive transformations, and the methoxy substituent can be demethylated or converted into other oxygenated substituents depending on the chosen reagent set. As a chiral amino acid intermediate in DL form, DL-4-Methoxyphenylglycine is suitable for stereochemical studies, racemate-to-enantiomer workflows, and downstream assembly of aromatic amino acid motifs in peptide and peptidomimetic frameworks.
1. Peptide Synthesis
DL-4-Methoxyphenylglycine is applied as an aromatic amino acid building block for peptide coupling chemistry where the amino group and carboxyl group enable amide bond formation under standard protected-amino-acid strategies. The phenylglycine scaffold supports incorporation into peptide sequences or peptide analogs, while the 4-methoxy substituent provides a stable handle for later side-chain functionalization or aromatic modification. Protection of the amine as a removable group and conversion of the carboxyl functionality into an activated ester or coupling-ready derivative can be used to control chemoselectivity during chain assembly. Incorporation of this residue into peptides can generate aromatic recognition elements for biochemical assays, fragment libraries, and peptidomimetic scaffolds that retain the stereochemical context of the starting racemate.
2. Chiral Resolution Studies
DL-4-Methoxyphenylglycine serves as a practical substrate for chiral synthesis workflows because the stereogenic center at the phenylglycine backbone is present as a racemic mixture. The methoxy-substituted aromatic side chain can be leveraged to form diastereomeric derivatives with chiral auxiliaries or chiral acids, facilitating separation of enantiomers when downstream enantiopure material is required. The amino acid functional groups enable derivatization into N-protected forms, esters, or salts that are compatible with resolution, analytical monitoring, and stereochemical assignment. Resulting enantiomerically enriched amino acid derivatives can then be used for stereodefined peptide construction and structure-activity relationship studies where absolute configuration impacts binding or conformational preferences.
3. Side-Chain Functionalization
DL-4-Methoxyphenylglycine is used in synthetic organic chemistry and medicinal chemistry intermediate preparation where the 4-methoxy aromatic motif can be transformed into alternative substitution patterns. The methoxy group can undergo demethylation to yield a phenolic handle, oxidation to more oxygenated aromatic derivatives, or substitution after appropriate activation, enabling systematic exploration of electronic and hydrogen-bonding effects. The amino acid backbone can be protected to allow selective manipulation of the aromatic ring while maintaining compatibility with subsequent deprotection and coupling steps. Downstream formation of modified aromatic amino acid derivatives supports peptidomimetic construction, SAR-focused reagent generation, and intermediate supply for larger heteroaryl or phenolic pharmacophore assemblies.
4. Bioconjugation Chemistry
DL-4-Methoxyphenylglycine can be incorporated into chemical biology workflows that require aromatic amino acid residues for conjugation-ready linkers and biomolecule labeling constructs. The amino acid functionality supports preparation of N-protected derivatives for controlled coupling to activated carboxylates, activated esters, or maleimide/haloacetamide-based electrophiles after appropriate functional group conversion. The aromatic ring with a methoxy substituent can contribute to hydrophobic and π-interaction characteristics in conjugates, supporting design of probes used for binding studies, affinity capture, or surface immobilization. Racemic starting material can be used when stereochemical purity is not the primary determinant, while resolution strategies can be applied when stereodependence is expected in biomolecular recognition.
5. Pharmaceutical Intermediate Preparation
DL-4-Methoxyphenylglycine is suitable for industrial and process chemistry as an amino acid-based intermediate toward aromatic peptidomimetic fragments and substituted phenylglycine derivatives used in fine chemical synthesis. The presence of an amino acid backbone enables conversion into N-protected intermediates, esterified forms, or activated carboxyl derivatives that can feed into coupling steps during route design. The methoxy-substituted aromatic ring provides a functional group pattern that can be carried through multi-step sequences and later adjusted to phenolic or other oxygenated substitution states as required by the target scaffold. Use of this racemate in manufacturing-oriented workflows can support scalable preparation of defined building blocks for medicinal chemistry programs and downstream API-adjacent intermediate supply chains.
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