4-Amino-L-Phenylalanine contains an L-configured α-amino acid backbone bearing a phenyl side chain substituted with an additional amino group at the 4-position, making it a ring-functionalized phenylalanine derivative. The molecule features a free α-amino group and a free carboxyl group suitable for peptide coupling, while the para-amino substituent on the aromatic ring provides a second primary amine for salt formation, hydrogen-bonding interactions, and further chemical derivatization. In biochemical and synthetic workflows, it is used as a defined building block to introduce an extra amine handle into peptides or peptide-related intermediates for conjugation, structure-activity studies, and analytical labeling strategies.
CAT No: CP10902
CAS No:943-80-6
Chemical Name:4-Amino-L-phenylalanine hydrate
4-Amino-L-Phenylalanine is an L-configuration amino acid featuring an additional primary amino group on the aromatic ring, making it a useful aniline-like building block for introducing extra nitrogen functionality into peptide and small-molecule frameworks. Its side-chain retains the stereochemical features of phenylalanine while providing a handle for further derivatization, including salt formation, coupling chemistry, and post-synthetic functional modification. In synthetic and medicinal chemistry workflows, this extra amine is leveraged to expand chemical diversity beyond standard phenylalanine derivatives.
1. Peptide Building Block
4-Amino-L-Phenylalanine is used as a non-standard amino acid building block for peptide synthesis when an extra side-chain amino functionality is required for downstream conjugation, salt formation, or additional derivatization of the assembled peptide. Researchers incorporate it into custom peptides and peptide libraries to introduce an additional nitrogen-bearing aromatic side chain that can participate in orthogonal chemical transformations after chain assembly. This makes it particularly relevant for workflows where the peptide scaffold must carry a functional group for later attachment to biomolecules, polymers, or surfaces, or where enhanced chemical handle density is needed for analytical derivatization.
2. Medicinal Chemistry Intermediates
4-Amino-L-Phenylalanine serves as a practical intermediate for medicinal chemistry programs that require an aromatic amino group positioned on a phenylalanine-like scaffold. Medicinal chemists and process development teams use it to access nitrogen-functionalized side chains that can be carried into peptidomimetics, kinase inhibitor fragments, and other small-molecule architectures where an aniline-type group is a key motif for further coupling or structure-activity relationship exploration. The amino acid backbone provides a well-defined stereochemical starting point, while the additional ring amine supports conversion into protected or activated derivatives used in iterative synthesis toward lead compounds.
3. Bioconjugation And Surface Coupling
4-Amino-L-Phenylalanine is commonly selected for bioconjugation and materials functionalization strategies that rely on an extra primary amine for coupling chemistry beyond the peptide backbone. Chemical biology groups use it to generate peptide conjugates or to build linkers that can be attached to activated surfaces and biomolecule scaffolds, enabling controlled introduction of nitrogen-rich functional sites for subsequent labeling or immobilization. The presence of the additional aromatic amine helps support derivatization routes where selective functional group availability is important for creating defined conjugation patterns in research-grade labeling workflows.
4. Analytical Derivatization Standard
4-Amino-L-Phenylalanine is also used in analytical method development and reference preparation when a nitrogen-functionalized aromatic amino acid is needed for derivatization-based quantification or for validating chromatographic and mass spectrometric behavior of amine-containing analytes. Analytical chemistry teams employ it to build calibration or derivatization sets that reflect the chemical reactivity of an aniline-like primary amine, supporting more realistic evaluation of sample preparation steps and detection workflows. Its L-configuration and defined functional group pattern make it a useful reference material for experiments where distinguishing amine reactivity and derivatization efficiency is critical.
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