4-Aminomethyl-L-Phenylalanine is an amino acid derivative featuring the L-phenylalanine backbone with an additional aminomethyl substituent on the para position of the phenyl ring, classifying it as a non-proteinogenic, side-chain functionalized aromatic amino acid. The molecule contains both an amino group and a carboxyl functional group on the α-carbon framework, while the para-aminomethyl side chain provides a second primary amine that can participate in protonation equilibria and serve as a chemical handle for further derivatization. In peptide and chemical biology workflows, it is used as a precursor for incorporating a tethered amine into peptide-like structures or for constructing conjugation-ready building blocks for labeling, crosslinking, or structure-activity studies.
CAT No: CP10601
4-Aminomethyl-L-Phenylalanine is an L-amino acid bearing a benzyl side chain substituted with an aminomethyl group, providing an additional primary amine beyond the standard α-amino functionality. This extra nucleophile makes the compound a practical building block for constructing amine-rich peptide fragments and for introducing orthogonally addressable nitrogen functionality during chemical biology workflows. Its stereodefined backbone supports downstream use in peptide assembly and in the preparation of amine-functionalized intermediates for conjugation and materials development.
1. Peptide Fragment Synthesis
4-Aminomethyl-L-Phenylalanine is used as a specialized amino acid building block for peptide synthesis when an extra side-chain primary amine is required at a defined residue position. Researchers incorporate it into custom peptides to generate amine-functionalized sequences for subsequent derivatization, such as attaching probes, affinity tags, or solubility-modulating groups without relying on post-synthetic installation at a less controlled site. The L-configuration supports stereochemically consistent incorporation into peptide architectures, while the aminomethyl substituent provides a handle for downstream coupling chemistry that is commonly exploited in peptide library and structure-property studies.
2. Bioconjugate Handle Preparation
4-Aminomethyl-L-Phenylalanine is frequently selected for preparing amine-reactive or amine-bearing intermediates used in bioconjugation workflows. The additional primary amine enables straightforward formation of amide or urea linkages with activated carboxylic acids and is also used to generate conjugation-ready derivatives for attaching peptides, small molecules, or biomolecule carriers. In chemical biology and protein chemistry, this functionality supports the design of conjugates where nitrogen-rich linkers improve labeling density control and provide defined attachment points for subsequent coupling to targeting ligands or biomolecular scaffolds.
3. Medicinal Chemistry Linker Building
4-Aminomethyl-L-Phenylalanine serves as a useful chiral building block in medicinal chemistry programs that require amine-containing linkers or amine-bearing pharmacophore scaffolds. Medicinal chemistry groups use it to construct peptidomimetic fragments and to introduce a second basic/functional nitrogen that can participate in salt formation, hydrogen-bonding interactions, or selective derivatization during lead optimization. The rigid phenylalanine-derived backbone combined with the aminomethyl side chain supports the synthesis of structured intermediates for SAR studies, where controlled placement of an additional amine is valuable for tuning physicochemical properties and enabling modular attachment strategies.
4. Amine-Functional Materials Development
4-Aminomethyl-L-Phenylalanine is applied in biomaterials and polymer-related research as a nitrogen-rich monomer or functional additive for generating amine-functional surfaces and networks. Materials scientists use its primary amine functionality to promote covalent immobilization, crosslinking, or surface coupling to substrates that present complementary reactive groups. This compound is particularly useful when researchers need a defined, chiral amino-acid-derived motif combined with an accessible aminomethyl handle to support subsequent material functionalization, including attachment of bioactive peptides or incorporation of capture chemistries for assay and separation platforms.
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