3-Amino-L-Phenylalanine is an L-configured, proteinogenic amino acid featuring a benzyl side chain that classifies it as a phenylalanine derivative with an additional amino substituent at the 3-position of the aromatic ring. The molecule contains a free α-amino group and a free α-carboxyl group while the aromatic ring bears a secondary amino functionality, enabling hydrogen bonding and potential sites for further derivatization under appropriate conditions. It is used as a chemically defined building block for preparing modified peptides and peptide analogues in chemical biology and protein engineering workflows, as well as for studying structure-property relationships and for generating aromatic amine handles for conjugation or analytical derivatization.
CAT No: CP10801
3-Amino-L-Phenylalanine is an L-configured amino acid featuring a benzyl side chain with an additional amino substituent on the aromatic ring, providing two amine functionalities for downstream derivatization. This structure makes it a useful building block for assembling substituted aromatic motifs in peptide-like scaffolds and for preparing nitrogen-rich intermediates used in medicinal chemistry and chemical biology workflows. As a free amino acid, it is typically handled as a research-grade reagent for coupling, labeling, and analytical standard development where aromatic amine chemistry is required.
1. Peptide And Amide Coupling
3-Amino-L-Phenylalanine is used as an amino acid building block when researchers need an aromatic diamine motif embedded into peptide fragments or peptide-like amides. Teams performing custom peptide synthesis and structure-activity relationship (SAR) studies often select this scaffold to introduce a ring-localized amino functionality that can be further functionalized after assembly, enabling late-stage diversification of side-chain chemistry. Its L-stereochemistry supports consistent incorporation into amino-acid-derived sequences during synthetic workflows where stereodefined residues are required.
2. Medicinal Chemistry Intermediates
3-Amino-L-Phenylalanine serves as a practical precursor for preparing substituted anilines, heterocycle precursors, and nitrogen-containing aromatic intermediates used in small-molecule discovery chemistry. Medicinal chemistry groups and contract research organizations commonly employ it to access aromatic amine substitution patterns that are difficult to obtain from simpler phenylalanine derivatives, supporting the construction of analog libraries for binding and property optimization. The presence of both an amino acid functional handle and an additional aromatic amine allows chemists to design stepwise derivatization strategies for downstream heterocycle formation and scaffold elaboration.
3. Chemical Biology Labeling Tools
3-Amino-L-Phenylalanine is frequently used in chemical biology workflows where an aromatic amine is required for conjugation to activated electrophiles or for incorporation into affinity-tagged or probe-like constructs. Researchers developing modified peptides, linkers, or nitrogen-rich capture reagents use the compound to introduce a defined aromatic amine site that can participate in selective coupling chemistries under standard laboratory conditions. This makes it a useful reagent when a stable, stereodefined amino acid backbone is paired with an additional functional group for downstream attachment to biomolecules or solid supports.
4. Analytical Standard Development
3-Amino-L-Phenylalanine is also used to prepare analytical standards and calibration materials for chromatographic and mass spectrometric workflows that target substituted phenylalanine derivatives. Analytical chemistry teams use it to validate retention behavior, confirm identity by MS/MS, and support quantitative method development when aromatic amine-containing amino acid species are expected. Because it contains a stereodefined amino acid core and a distinct aromatic amine signature, it provides a structurally relevant reference point for assay optimization and impurity profiling in amino-acid-derived synthesis and derivatization studies.
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