3-(4-Pyridyl)-D-Alanine is a D-amino acid derivative featuring an alanine backbone bearing a 4-pyridyl substituent on the side chain, classifying it as a non-proteinogenic, aromatic heterocycle-containing amino acid. The molecule contains a free amino group and a free carboxyl group, with the side chain presenting a pyridine nitrogen that can participate in hydrogen bonding and coordinate metal ions while maintaining the stereochemical identity indicated by the "D" prefix. It is used as a defined building block for peptide and peptidomimetic synthesis and as a chemical handle for structure-activity studies, molecular labeling, and coordination-based materials or analytical method development where the pyridyl functionality provides a site for interaction.
CAT No: CP23002
3-(4-Pyridyl)-D-Alanine is a D-configured amino acid featuring a 4-pyridyl side chain that provides a basic, aromatic nitrogen for coordination and physicochemical tuning. This structure makes it a useful building block for designing peptide and peptidomimetic motifs where metal-binding or heteroaromatic recognition is required, while the D-stereochemistry supports incorporation into frameworks that benefit from stereochemical control. In research settings, it is commonly handled as a defined amino acid intermediate for chemical biology probes, ligand development, and analytical reagent preparation where the pyridyl functionality is central.
1. Peptidomimetic Ligand Design
3-(4-Pyridyl)-D-Alanine is used to introduce a 4-pyridyl side chain into peptide-like scaffolds for ligand and peptidomimetic development, including constructs aimed at studying heteroaromatic recognition and metal coordination behavior. Researchers in medicinal chemistry and chemical biology often incorporate this D-amino acid to control stereochemistry at the residue level while leveraging the pyridine nitrogen as a coordination site or interaction handle. The defined amino acid functionality supports downstream coupling strategies for assembling short peptides, constrained analogs, and SAR-focused libraries where the pyridyl group is the key structural element.
2. Metal-Binding Probe Development
3-(4-Pyridyl)-D-Alanine is frequently selected for probe construction and affinity reagent development where the 4-pyridyl group serves as a predictable binding motif. Chemical biology groups use pyridyl-containing amino acid residues to create small-molecule or peptide-based reporters that can interact with metal ions or metal-containing targets, enabling studies of coordination chemistry in a biologically compatible format. The D-configuration is particularly useful when researchers want to reduce stereochemical ambiguity in the probe scaffold and maintain consistent spatial presentation of the pyridyl side chain during conjugation and assay development.
3. Analytical Standard and LC-MS Workflows
3-(4-Pyridyl)-D-Alanine is applied as a defined amino acid standard and reference component in analytical method development, especially when quantifying pyridyl-containing amino acid motifs or monitoring synthetic intermediates and peptide fragments by LC-based workflows. Analytical chemists and pharmaceutical intermediate developers use it to support calibration, retention-time verification, and identity confirmation for compounds containing the 4-pyridyl functionality. Because the compound is a discrete, stereochemically defined building block, it is also useful for quality control of peptide synthesis outputs where the presence and integrity of the pyridyl-bearing residue must be verified.
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