4-Aminomethyl-D-Phenylalanine is a D-configured amino acid derivative featuring a phenylalanine backbone bearing an additional aminomethyl substituent at the 4-position of the side chain. The molecule contains a free primary amino group on the side chain and an amino and carboxyl functional group typical of amino acids, with the extra aminomethyl functionality providing a second nucleophilic handle for salt formation, derivatization, and side-chain functionalization. In synthesis and chemical biology workflows, it is used as a building block for preparing modified peptides and conjugates where an extra amine enables attachment of labels, linkers, or reactive groups for structure-activity studies and molecular labeling.
CAT No: CP10602
4-Aminomethyl-D-Phenylalanine is a D-configured phenylalanine analog bearing an aminomethyl substituent on the side chain, providing an additional primary amine for orthogonal functionalization and downstream coupling chemistry. This non-proteinogenic amino acid building block is frequently used in peptide and peptidomimetic design where a controllable, cationic handle is needed for salt formation, linker installation, or side-chain derivatization. Its stereochemical definition supports reproducible structure-activity and conformational studies in synthetic peptide frameworks.
1. Peptidomimetic Building Blocks
4-Aminomethyl-D-Phenylalanine is used as a side-chain functional amino acid building block for constructing peptidomimetics and modified peptide scaffolds in medicinal chemistry and chemical biology programs. The appended aminomethyl group enables attachment of solubilizing motifs, tethering elements, or additional pharmacophore fragments after peptide assembly, supporting iterative structure-activity relationship workflows. Researchers also select the D-configuration to introduce stereochemical control and to probe how inversion at the amino acid center affects conformation, receptor/target recognition patterns, or overall scaffold behavior in synthetic libraries.
2. Bioconjugation Linker Installation
4-Aminomethyl-D-Phenylalanine serves as a practical intermediate for generating amine-functionalized peptide conjugates and biomolecule linkers. The extra primary amine can be used to introduce defined attachment points for coupling to activated carboxylates, activated esters, or other electrophilic conjugation partners during bioconjugate workflows, including antibody/ligand conjugate development and affinity reagent preparation. In these applications, the amino acid's defined stereochemistry and amino acid backbone compatibility help maintain consistent geometry within the conjugation handle, which is useful for reproducible labeling densities and comparative studies across conjugate series.
3. Pharmaceutical Intermediate Development
4-Aminomethyl-D-Phenylalanine is commonly employed as a chiral amino acid intermediate for the synthesis of amine-rich fragments used in pharmaceutical intermediate pipelines. The side-chain aminomethyl functionality provides a versatile platform for further derivatization into protected amines, salt forms, or coupling-ready intermediates, supporting downstream assembly of drug-like molecules and peptidomimetic candidates. Process and development teams value this building block when a stereodefined, additional amine handle is required to enable late-stage functionalization strategies and to support parallel synthesis of analog series.
4. Chemical Biology Probe Synthesis
4-Aminomethyl-D-Phenylalanine is used to build chemical biology probes and tagged peptide reagents where an extra primary amine is needed for installing detection or enrichment features. In probe construction workflows, the aminomethyl group supports attachment of affinity tags, solubilizing groups, or reporter moieties through amide or other amine-reactive coupling chemistries, while the D-amino acid center helps maintain stereochemical integrity in probe libraries. This makes the building block particularly useful for preparing structurally consistent probe variants for binding studies, target engagement experiments, or analytical enrichment formats in research settings.
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