4-Amino-D-Phenylalanine is a D-configured amino acid derivative belonging to the phenylalanine family, featuring a benzyl side chain substituted with an additional amino group at the para (4-) position. The molecule contains both an α-amino group and an α-carboxyl group, and its side chain presents a primary aniline-like functionality that can participate in hydrogen bonding and acid-base behavior while remaining chemically distinct from the unsubstituted phenylalanine aromatic ring. As a nonstandard amino acid for peptide and structure-activity studies, it can be used as a substrate building block to introduce the para-aminophenyl functionality into peptide frameworks or to support chemical labeling and conjugation strategies through the side-chain amino handle.
CAT No: CP10901
CAS No:102281-45-8
Synonyms/Alias:102281-45-8;4-Amino-D-phenylalanine;(R)-2-Amino-3-(4-aminophenyl)propanoicacid;D-4-Aminophenylalanine;(2R)-2-amino-3-(4-aminophenyl)propanoicacid;SBB064108;D-4-aminophe;AC1LOQYL;p-Amino-D-phenylalanineacid;SCHEMBL288375;CTK8C4803;MolPort-001-758-809;ZINC4222913;ANW-73164;CA-674;AC-5869;AM82696;AJ-49128;AK106107;KB-36522;O026;TL8000119;TX-017507;ST24035312;I01-5162
4-Amino-D-Phenylalanine is a D-configured phenylalanine analog bearing an additional amino substituent at the 4-position of the aromatic ring, providing a distinct side-chain reactivity profile compared with proteinogenic phenylalanine. This amino-functionalized aromatic scaffold is commonly used as a chiral amino acid building block for constructing peptidomimetic structures and for introducing an aniline-type handle into peptide and small-molecule frameworks. Its stereodefined D-configuration supports applications where conformational and stereochemical control are important for downstream structure-activity and stability studies.
1. Peptidomimetic Building Block
4-Amino-D-Phenylalanine is used by medicinal chemistry and peptide research groups to incorporate a stereodefined D-amino acid residue into peptidomimetic scaffolds, enabling systematic SAR (structure-activity relationship) studies where backbone stereochemistry and side-chain electronics are varied. The extra aromatic amino group provides a functional site for further derivatization during lead optimization, such as tuning hydrogen-bonding capacity and enabling late-stage coupling to electrophiles or acylating/alkylating reagents. This makes the compound a practical building block for generating libraries of modified peptide-like structures used in hit-to-lead workflows and chemical biology probe development.
2. Modified Peptide Synthesis
4-Amino-D-Phenylalanine serves as a specialized amino acid building block for custom peptide synthesis when researchers need a D-amino acid residue combined with an additional aromatic amine for downstream functionalization. Peptide synthesis teams use it to prepare peptides and peptide conjugates where the aromatic amino substituent can be used as a chemical handle for post-assembly modification, including attachment of solubilizing groups, linkers, or affinity tags. The D-stereochemistry supports preparation of stereochemically defined peptide analogs used in studies of structure, conformation, and chemical stability, particularly where non-natural stereocenters are introduced to modulate properties of peptide backbones.
3. Pharmaceutical Intermediate Development
4-Amino-D-Phenylalanine is applied in pharmaceutical intermediate development as a chiral, functionalized amino acid precursor for assembling aromatic amine-containing fragments. Process development and custom synthesis laboratories often select this scaffold when a stereodefined D-amino acid motif must be carried into a later-stage intermediate, while the additional aniline-type functionality offers a convenient point for conversion into protected derivatives or coupling-ready forms. This supports the preparation of diverse small-molecule intermediates used in medicinal chemistry programs, where controlling both chirality and aromatic substitution patterns is critical to achieving consistent synthetic outcomes across analog series.
4. Chemical Biology Conjugation Handles
4-Amino-D-Phenylalanine is used to introduce an additional aromatic amine into bioactive or biointerface-relevant molecules, supporting chemical biology workflows that require a robust, derivatizable functional group. Researchers employ this amino acid building block to generate peptide-based or peptide-derived constructs that can be further functionalized for conjugation strategies, including formation of amide or urea linkages and attachment to carrier molecules or immobilization surfaces. The combination of a D-amino acid backbone and an extra aromatic amino handle makes it useful for constructing stereochemically defined conjugates used in binding studies, localization assays, and materials-oriented chemical biology experiments where controlled functional-group placement matters.
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