2-Amino-D-Phenylalanine is a D-stereochemical, non-natural amino acid featuring a benzyl side chain characteristic of phenylalanine derivatives and a backbone bearing both amino and carboxyl functional groups. The molecule contains a free α-amino group and a free carboxylic acid, with the D configuration indicated by the product name, which influences conformational preferences and peptide stereochemical outcomes. It is used in peptide synthesis and structure-activity or stereochemical studies where incorporation of a D-configured phenylalanine analogue supports conformational probing, analog generation, and analytical method development for stereochemically defined amino acid building blocks.
CAT No: CP10702
2-Amino-D-Phenylalanine is a D-configured phenylalanine analog featuring a stereochemically defined chiral center at the alpha carbon and a hydrophobic benzyl side chain typical of aromatic amino acids. As a non-proteinogenic, stereochemically pure amino acid building block, it is commonly used in peptide and peptidomimetic synthesis to introduce D-amino acid character, which is valuable for controlling backbone stereochemistry and improving chemical robustness in synthetic sequences. Its free amino functionality and carboxylic acid group make it a practical starting material for downstream derivatization into peptide-coupling-ready formats and for constructing defined chiral intermediates in medicinal chemistry research.
1. D-Peptide Building Block
2-Amino-D-Phenylalanine is widely used by peptide chemists and medicinal chemistry groups to incorporate D-phenylalanine stereochemistry into short peptides, peptidomimetics, and stereodefined sequence variants. The D-configuration at the backbone provides a straightforward way to generate peptides with altered conformational preferences and proteolytic stability trends compared with all-L analogs, supporting structure-property studies and lead optimization workflows. In practice, it is selected when a defined aromatic side chain is needed alongside D-amino acid stereocontrol for sequence-level SAR (structure-activity relationship) experiments.
2. Peptidomimetic Medicinal Chemistry
2-Amino-D-Phenylalanine supports medicinal chemistry programs focused on designing conformationally and stereochemically controlled peptidomimetics. Researchers use this D-amino acid building block to construct analog series where backbone stereochemistry is systematically varied while maintaining an aromatic hydrophobic side chain, enabling clearer interpretation of how stereochemical changes influence biological assay readouts. The compound's simple aromatic functionality also makes it a convenient precursor for preparing further substituted derivatives used in SAR libraries and in the synthesis of constrained or backbone-modified analogs.
3. Chiral Intermediate Development
2-Amino-D-Phenylalanine is frequently employed in chemical development settings to generate chiral intermediates for subsequent functionalization and coupling chemistry. Its well-defined D stereocenter and aromatic side chain provide a reliable starting point for preparing protected amino acid derivatives, activated ester forms, or other coupling-ready intermediates used in custom synthesis. This makes it particularly relevant for teams developing stereochemically defined building blocks for research-scale library synthesis, where maintaining enantiopurity and structural fidelity across intermediates is essential for downstream characterization and comparability.
4. Analytical Reference Material
2-Amino-D-Phenylalanine is also used by analytical and method-development laboratories as a stereochemically defined reference in chiral separation and amino acid profiling workflows. Because D- and L- stereoisomers can be distinguished by appropriate chromatographic or derivatization strategies, having a pure D-phenylalanine analog supports method validation, calibration, and identification of stereochemical variants in complex samples. This is especially useful when researchers need defined standards to confirm the presence of D-amino acid residues in synthetic peptides, degradation studies, or stereochemical impurity assessments.
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