4-Aminomethyl-DL-Phenylalanine is an amino acid derivative featuring a phenylalanine backbone bearing an additional aminomethyl substituent at the 4-position of the aromatic side chain, placing it in the class of non-proteinogenic, side-chain-functionalized amino acids. The molecule contains both an amino group and a carboxyl group characteristic of amino acid frameworks, and the "DL" designation indicates a racemic mixture of stereoisomers at the chiral center associated with the phenylalanine portion. As a chemically defined building block, it is used in peptide and conjugate synthesis to introduce a pendant primary amine for subsequent derivatization, crosslinking, or incorporation into structure-activity and labeling studies where an extra nucleophilic handle is required.
CAT No: CP10603
4-Aminomethyl-DL-Phenylalanine is an amino acid derivative featuring a phenylalanine backbone bearing an additional aminomethyl side chain, provided as a DL (racemic) mixture. This extra primary amine increases chemical handle density relative to standard phenylalanine derivatives and makes the compound useful for downstream derivatization, including attachment to activated surfaces, polymers, or biomolecular scaffolds. Its amino-functional structure also supports its role as a practical building block in medicinal chemistry and peptide-related intermediate development where controlled introduction of an additional nitrogen functionality is required.
1. Peptide Building Block Intermediates
4-Aminomethyl-DL-Phenylalanine is used as a specialty amino acid building block for preparing modified peptide segments and peptide-like intermediates that require an extra primary amine for later functionalization or conjugation. Researchers developing amine-rich peptide analogs, side-chain elaborated sequences, or branching/functionalized peptide motifs rely on the aminomethyl group as a convenient site for subsequent coupling to electrophiles, activated esters, or carbonyl-derivatized handles. The DL stereochemical mixture is often selected during early-stage library synthesis and intermediate screening workflows where stereochemical resolution is handled downstream or where relative reactivity and functional-group tolerance are the primary priorities.
2. Bioconjugation And Surface Coupling
4-Aminomethyl-DL-Phenylalanine serves as a nitrogen-rich linker component for bioconjugation and surface immobilization strategies in chemical biology and biomaterials research. The additional primary amine enables straightforward formation of amide or urea-type linkages with activated carboxylic acids or carbonyl-reactive partners, supporting attachment to carrier proteins, polymer backbones, or functionalized resins used for affinity capture and reagent immobilization. Because the compound provides an extra conjugation handle beyond a typical amino acid side chain, it is frequently selected when a higher local density of reactive sites is beneficial for constructing multivalent conjugates, immobilized ligands, or amine-functional coatings for downstream assays and material characterization.
3. Medicinal Chemistry Side-Chain Functionalization
4-Aminomethyl-DL-Phenylalanine is commonly employed in medicinal chemistry programs as a chiral-independent amino acid-derived intermediate for introducing an aminomethyl functionality into small-molecule scaffolds and peptidomimetic designs. Medicinal chemistry and process-development teams use the compound to access analog series where an additional basic nitrogen is used to tune physicochemical properties, improve synthetic modularity, or provide a handle for late-stage derivatization. The racemic (DL) form is particularly practical for route scouting and intermediate supply during SAR exploration, where the immediate need is reliable access to the functional group pattern rather than stereodefined stereochemistry at the earliest synthetic stage.
4. Polymer And Biomaterials Functional Units
4-Aminomethyl-DL-Phenylalanine is applied as an amine-functional building unit for preparing functional polymers and biomaterial precursors that require primary amine incorporation. Biomaterials groups use the aminomethyl side chain to introduce reactive nitrogen sites for subsequent crosslinking, grafting, or coupling to complementary chemistries used in hydrogel formation, surface modification, and scaffold functionalization. In these workflows, the compound's amino-rich structure helps create materials with defined chemical reactivity for immobilizing bioactive ligands, tuning charge density, or enabling stepwise post-functionalization during material development and characterization.
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