L-4-Aminophenylglycine is an L-configured, non-proteinogenic amino acid featuring a glycine backbone substituted with a para-aminophenyl side chain, placing an aniline-type primary amine on the aromatic ring. The molecule contains both an amino group and a carboxylic acid functional group, with the additional aromatic amino substituent providing a second site for protonation and potential derivatization under appropriate conditions. In peptide and amino acid derivative synthesis, it functions as a building block for introducing an aniline-bearing aryl side chain into peptide analogues for structure-activity studies, conjugation handle installation, and chemical biology labeling strategies.
CAT No: CP09902
L-4-Aminophenylglycine is an L-configured amino acid featuring a glycine backbone substituted with a para-aminophenyl group, giving a chiral center at the alpha carbon and a second primary amine on the aromatic ring. The molecule contains both an alpha-amino functionality and a carboxylic acid group, enabling standard amino acid coupling chemistry, while the aniline-like side-chain amine introduces additional reactivity for derivatization and orthogonal protection strategies. Aromatic conjugation and the additional amine can influence solubility, salt formation, and chemoselective transformations during protected amino acid synthesis. As a chiral amino acid intermediate and peptide-relevant building block, L-4-Aminophenylglycine can be incorporated into peptide frameworks or converted into functionalized derivatives for downstream synthetic and biochemical studies.
1. Peptide Synthesis
L-4-Aminophenylglycine is applied in peptide synthesis as a chiral amino acid building block whose alpha-amino and carboxylic acid groups support amide bond formation under protected amino acid coupling conditions. The para-aminophenyl side chain introduces a second nucleophile that can be selectively protected (for example, as an aniline-compatible protecting group) to maintain chemoselectivity during N-protection, activation, and coupling. Incorporation into peptide chains can enable aromatic side-chain display for receptor-binding studies, scaffold stabilization, or conformational tuning in peptidomimetic construction. Downstream deprotection can regenerate the free aromatic amine for further conjugation or for generating peptide analogs with tunable charge and hydrogen-bonding patterns.
2. Chemical Biology Probes
L-4-Aminophenylglycine is used in chemical biology and molecular labeling workflows where the aromatic primary amine serves as a handle for bioconjugation and probe diversification. The presence of both an amino acid backbone and a para-amine allows preparation of tagged derivatives such as amide-linked, urea/thiourea-forming, or reductive amination products after appropriate orthogonal protection of the alpha-amino functionality. Chiral retention at the alpha carbon supports stereochemically defined probe libraries for studying binding preferences, while the aromatic ring can participate in π-stacking and hydrogen-bond interactions. Resulting derivatives can function as research intermediates for affinity reagents, enzyme-binding ligands, or structure-defined chemical probes compatible with peptide-derived scaffolds.
3. SAR Studies And Scaffold Design
L-4-Aminophenylglycine is relevant to structure-activity relationship studies and fragment-based scaffold design because it provides a stereodefined aromatic amino acid motif with an additional functional group for systematic variation. The para-aminophenyl side chain enables controlled modification into substituted anilines, sulfonamides, heteroatom-containing linkers, or cyclization precursors, while the carboxylate and alpha-amino groups allow incorporation into peptide-like frameworks. Side-chain derivatization can modulate basicity, hydrogen-bond donor/acceptor balance, and aromatic electronics, supporting iterative synthesis of analog series around a consistent chiral core. Downstream, the compound can serve as a chiral intermediate for generating SAR-ready libraries and for preparing defined stereochemical variants used in comparative binding and specificity studies.
4. Protected Amino Acid Intermediate
L-4-Aminophenylglycine is employed as a chiral intermediate in protected amino acid synthesis where orthogonal protection of the two amines is central to maintaining coupling control. The alpha-amino group can be protected for peptide coupling, while the aromatic primary amine can be protected with an aniline-compatible strategy to prevent side reactions during activation of the carboxyl group and formation of amide bonds. The stereogenic center supports preparation of enantiopure derivatives for stereochemical studies, including peptide building block preparation and C-terminal or N-terminal functionalization. Resulting protected derivatives can be used to manufacture peptide analogs, generate defined intermediates for fine chemical synthesis, and support downstream deprotection steps that reveal the aromatic amine for conjugation or further functional group transformation.
5. Pharmaceutical Intermediate Preparation
L-4-Aminophenylglycine is suitable for pharmaceutical intermediate preparation in synthetic organic chemistry where a chiral amino acid core with an aniline-like handle can be transformed into drug-like fragments. The carboxylic acid and protected amine functionality can participate in standard medicinal chemistry sequences such as amide formation, salt formation, and conversion to activated derivatives, while the para-amine can be functionalized into heterocycles, sulfonamides, or aromatic linkers. The aromatic amine's reactivity supports downstream coupling to electrophiles used in medicinal chemistry, enabling construction of stereodefined scaffolds that incorporate amino acid-derived motifs. Industrially, the compound's structure supports process-oriented intermediate generation for producing defined stereochemical building blocks used in specialty chemical production and route development.
6. Analytical And Reference Standards
L-4-Aminophenylglycine is applied in analytical research and method development as a chiral reference material and derivatization substrate for amino acid profiling. The combination of an alpha-amino acid framework and a para-aminophenyl group enables formation of diagnostic derivatives for chromatographic separation or mass spectrometric detection after controlled protection and derivatization. Stereochemical definition at the alpha carbon supports enantiomer-resolved analysis when paired with suitable chiral derivatization strategies or chiral separation methods. Downstream use includes preparation of calibration or qualification materials for monitoring amino acid incorporation in peptide synthesis workflows and for verifying identity of intermediate streams in applied process chemistry.
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