D-4-Aminophenylglycine is a non-proteinogenic amino acid derivative featuring a phenylglycine scaffold with a para-positioned aniline (4-aminophenyl) side chain and a glycine-like backbone bearing both an amino group and a carboxyl group. The molecule is specified as the D-stereoisomer and presents a primary aniline functionality that can participate in hydrogen bonding and can be chemically modified for conjugation or further derivatization, while the backbone amino and carboxyl groups provide the typical sites for salt formation and peptide-coupling chemistry. In peptide and chemical biology research, D-4-Aminophenylglycine is used as a building block to introduce an aromatic, aniline-bearing side chain into synthetic peptides, enabling structure-activity studies, labeling strategies, and the preparation of more complex amino acid and peptide derivatives.
CAT No: CP09903
D-4-Aminophenylglycine is a D-configured amino acid featuring a benzyl-like phenyl ring substituted at the para position with an aniline-type amino group and linked through a glycine methylene to the stereogenic alpha carbon. The molecule contains a primary aniline on the aromatic ring alongside the alpha-amino and alpha-carboxyl functionality, enabling orthogonal chemoselective transformations that distinguish side-chain and backbone reactivity. The D stereochemistry supports stereochemically defined incorporation into peptide-like scaffolds and chiral derivatization strategies, while the aromatic amine can participate in nucleophilic substitution, diazotization/azo coupling, or protection-deprotection sequences during synthetic planning. D-4-Aminophenylglycine is commonly handled as a chiral amino acid intermediate for building peptide analogs, SAR-focused libraries, and downstream functional materials where an aniline handle is retained or transformed.
1. Peptide Synthesis
D-4-Aminophenylglycine is applicable to peptide building block preparation where a D-amino acid residue is incorporated to tune backbone stereochemistry and side-chain electronics. The alpha-carboxylic acid and alpha-amino group support standard peptide coupling chemistry, while the para-aniline side chain can be protected to prevent undesired acylation or crosslinking during chain assembly. The aromatic amine enables controlled deprotection after coupling to yield a free aniline for subsequent conjugation, labeling, or aromatic functionalization. Peptide science applications may include generating D-amino acid-containing analogs for stability studies and scaffold diversification in solid-phase or solution-phase workflows.
2. Side-Chain Functionalization
D-4-Aminophenylglycine is suited for amino acid derivatization strategies that exploit the para-aniline functionality as a synthetic handle for functional group interconversion. The aromatic primary amine can be selectively protected (e.g., via amine-protecting groups) during backbone manipulations and later converted into amides, ureas, sulfonamides, azo linkages, or heteroaryl substituents through established electrophile and coupling chemistries. The D-configured alpha center allows stereodefined analog synthesis, which is particularly relevant when the stereochemistry of the amino acid residue influences conformational preferences and binding-site recognition. Downstream use can include constructing functionalized peptidomimetics, fluorescent or affinity-tagged derivatives, and intermediate platforms for further medicinal chemistry transformations.
3. Drug Discovery SAR Studies
D-4-Aminophenylglycine supports structure-activity relationship studies in medicinal chemistry by providing a chiral, aromatic amino acid motif with a para-amino substituent for electronic and interaction tuning. The phenylglycine framework can be incorporated into peptide-like inhibitors or constrained scaffolds, while the aniline side chain enables systematic variation through derivatization to probe hydrogen-bonding capacity, aromatic stacking, and steric effects. The D stereochemistry can be used to map stereochemical requirements and to generate matched pairs of stereoisomeric analogs for SAR interpretation. The compound's reactivity profile also supports iterative library synthesis where protected amino acid intermediates are converted into diversified final structures for screening campaigns.
4. Bioconjugation Chemistry
D-4-Aminophenylglycine is suitable for chemical biology workflows that require an aniline-bearing amino acid motif for conjugation and labeling strategies. The para-amino group can be transformed into electrophilic or coupling-ready derivatives, enabling attachment to carriers, linkers, or biomolecule-reactive scaffolds while the backbone amine and carboxyl group can be managed through protection to maintain chemoselectivity. The D stereocenter can help control the spatial presentation of the aromatic side chain in conjugates, which may influence binding behavior in affinity assays or immobilization formats. Downstream applications include preparing amino-acid-based linkers for biomolecule labeling, generating conjugation intermediates for assay reagents, and producing defined peptidomimetic probes.
5. Pharmaceutical Manufacturing Intermediates
D-4-Aminophenylglycine is used as a chiral amino acid intermediate in fine chemical and pharmaceutical manufacturing contexts where controlled stereochemistry and functional group retention are required. The presence of both backbone functional groups and a para-aniline side chain enables manufacturing route design that incorporates orthogonal protection strategies, allowing peptide coupling steps and later conversion of the aniline into specification-defined derivatives. The aromatic amine can be carried through as a protected functionality to minimize side reactions during scale-up, then deprotected or transformed to meet downstream intermediate specifications. The compound can therefore serve in industrial synthesis of peptide analogs, chiral building blocks for medicinal chemistry, and process intermediates that feed into larger, functionalized molecular targets.
6. Analytical Research Standards
D-4-Aminophenylglycine can function as a stereochemically defined analytical reference and derivatization substrate for method development in amino acid and peptide analysis. The combination of a D-configured alpha center and a para-aniline side chain enables formation of detectable derivatives for chromatographic or spectrometric workflows, including derivatization schemes that exploit aromatic amine reactivity. The compound's defined structure supports calibration and identity confirmation for protected amino acid derivatives, peptide fragments, and degradation products where stereochemistry and side-chain functionality must be distinguished. Broader analytical use can extend to quality control of peptide building block preparations and monitoring of side-chain modification states in synthetic intermediate streams.
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