3-(3-Pyridyl)-D-alanine is a non-proteinogenic, aromatic amino acid derivative featuring a D-configured α-amino acid backbone bearing a 3-pyridyl substituent on the side chain. The molecule contains a free primary amino group and a carboxyl group, with the side chain presenting a heteroaromatic pyridine ring that can participate in metal coordination and pH-dependent protonation. It is used as a defined building block for peptide and peptidomimetic synthesis and for structure-activity or binding studies where an amino acid analogue with a pyridine functional handle is needed for chemical labeling, conjugation, or analytical method development.
CAT No: CP22902
3-(3-Pyridyl)-D-alanine is a D-configured amino acid bearing a 3-pyridyl substituent on the side chain, providing a built-in aromatic nitrogen for coordination and physicochemical tuning. This non-proteinogenic amino acid is commonly used as a chemically defined building block in peptide and peptidomimetic design where side-chain basicity and metal-binding behavior are leveraged for downstream structure-function studies. Researchers also use it as a stereochemically defined ligand-like amino acid unit for synthetic intermediate development and analytical method work where the pyridyl group serves as a handle for derivatization and detection.
1. Peptidomimetic Building Blocks
3-(3-Pyridyl)-D-alanine is used by medicinal chemistry and chemical biology groups to introduce a stereodefined, pyridyl-bearing residue into peptides and peptidomimetics. The D-configuration and the 3-pyridyl side chain help modulate local conformation and provide an aromatic nitrogen that can participate in metal coordination or polar interactions, which is valuable in structure-activity relationship (SAR) studies and binding-mode investigations. In practice, it is selected when a defined side-chain donor/acceptor pattern is desired without relying on proteinogenic residues, and when the pyridyl functionality is expected to remain chemically accessible for later derivatization or conjugation steps.
2. Metal-Binding Probe Design
3-(3-Pyridyl)-D-alanine is applied in materials and chemical biology workflows that require amino acid-derived ligands with a built-in 3-pyridyl coordination site. The pyridine nitrogen enables rational design of coordination complexes or coordination-driven assembly in peptide-based scaffolds, polymer conjugates, and surface-immobilized systems where controlled binding to metal ions is needed for structural stabilization or functional readouts. Researchers favor this scaffold because it combines an amino acid backbone with a single, well-defined aromatic donor, allowing reproducible incorporation into larger constructs while maintaining stereochemical control from the D-amino acid framework.
3. Pharmaceutical Intermediate Development
3-(3-Pyridyl)-D-alanine is also used as a stereochemically defined intermediate in the preparation of heteroaryl-containing building blocks for pharmaceutical and agrochemical chemistry. The 3-pyridyl group provides a synthetically useful aromatic handle for further functionalization, enabling downstream construction of substituted pyridines, ligand motifs, or protected heteroaryl amino acid derivatives used in medicinal chemistry campaigns. Teams developing complex small molecules often select this amino acid because it offers a ready-made chiral amino acid platform paired with a functional aromatic ring, supporting streamlined synthesis of advanced intermediates for library generation and SAR exploration.
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