2-Amino-L-Phenylalanine is a free, proteinogenic amino acid with an L-configuration at the alpha carbon and a benzyl side chain characteristic of phenylalanine. The molecule contains both an amino group at the alpha position and a carboxyl functional group, with the aromatic phenyl ring on the side chain providing hydrophobic character and the ability to participate in π-interactions. As a substrate building block for peptide synthesis and amino acid derivative preparation, it can be used in solution-phase or solid-phase coupling workflows and in analytical or labeling studies where the unprotected amino and carboxyl groups are required for further chemical transformations.
CAT No: CP10701
2-Amino-L-Phenylalanine is an L-configuration amino acid featuring a phenyl side chain and an additional amino substituent on the alpha position, making it a valuable nitrogen-rich building block for peptide and peptidomimetic chemistry. Its dual amine functionality supports downstream derivatization and incorporation into chemically defined structures where controlled amine presentation is needed. In research workflows, it is commonly selected to introduce an extra amino group for subsequent coupling, functionalization, or analytical labeling strategies.
1. Peptidomimetic Building Block
2-Amino-L-Phenylalanine is used by peptide and peptidomimetic chemists to introduce an additional amino functionality adjacent to the backbone, enabling the construction of modified peptide analogs and nitrogen-enriched scaffolds. Researchers typically employ it in solution-phase or solid-phase assembly workflows where site-specific incorporation of an extra amine can support subsequent derivatization steps, such as attachment of solubilizing groups, conjugation handles, or orthogonally protected functionalities for stepwise elaboration. The L-stereochemistry and phenyl side chain provide a familiar chiral amino acid framework while the extra amino group expands the chemical space accessible for structure-activity relationship studies and chemical biology probes.
2. Bioconjugation Handle Development
2-Amino-L-Phenylalanine is applied in bioconjugation and chemical biology workflows where an additional primary amine is required to install conjugation sites onto peptides, linkers, or protein-reactive constructs. Teams developing antibody-peptide conjugates, affinity probes, or immobilized peptide reagents often use this amino acid as a defined intermediate to tune the density and positioning of amine groups on the final conjugate. The presence of two amino functionalities supports controlled downstream coupling strategies to biomolecules and surfaces, including preparation of standardized conjugation reagents for screening and assay development, while maintaining a chemically well-defined building block for reproducible reagent manufacturing.
3. Pharmaceutical Intermediate Synthesis
2-Amino-L-Phenylalanine is frequently selected as a pharmaceutical intermediate building block for nitrogen-rich heterocycle and amine-functionalized fragment synthesis in medicinal chemistry programs. Process development and synthetic chemistry groups use it to access scaffolds where an extra amino group is required for further functional group interconversions, salt formation, or incorporation into larger drug-like structures. Its chiral L-configuration and phenylalanine-derived side chain provide a convenient stereochemical motif for building stereodefined intermediates, supporting downstream elaboration toward peptidomimetic candidates, amide-rich fragments, and other amine-bearing intermediates used in lead optimization campaigns.
4. Chiral and Nitrogen-Rich Standards
2-Amino-L-Phenylalanine is also used for preparing chemically defined analytical standards and reference materials in LC-based and derivatization-dependent quantification workflows, particularly when an extra amino group is the feature being monitored or normalized. Analytical chemistry teams may incorporate it into calibration strategies for amine-containing species, method development for amino acid derivative detection, or validation of derivatization efficiency where primary amines are converted into detectable derivatives. Because it is a stereodefined L-amino acid with an additional amine functionality, it serves as a useful reference point for experiments that require nitrogen-rich amino acid analogs rather than conventional single-amine amino acids.
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