3-(4-Pyridyl)-L-Alanine is an L-alanine derivative in which the side chain bears a 4-pyridyl substituent, replacing the native methyl group with a heteroaromatic ring. The molecule contains a free amino group and a free carboxyl group characteristic of amino acids, and the pyridine nitrogen provides a basic heteroatom for coordination and acid-base behavior while the indicated L-stereochemistry defines the chiral center. As a nonstandard amino acid building block, it is used in peptide and peptidomimetic synthesis to introduce a pyridyl functional handle for structure-activity studies, metal-binding motif incorporation, and analytical labeling or conjugation workflows.
CAT No: CP23001
3-(4-Pyridyl)-L-Alanine is an L-amino acid bearing a 4-pyridyl aromatic side chain, providing a basic heteroaromatic functionality that can participate in coordination chemistry and site-specific interactions. This structure makes it a useful building block for constructing peptide and small-molecule frameworks where a pyridine handle is required for binding, metal coordination, or physicochemical tuning. Researchers also use this amino acid as a defined chiral component for synthetic programs that need a heteroaromatic side chain with predictable reactivity.
1. Peptide Building Block Use
3-(4-Pyridyl)-L-Alanine is used in peptide synthesis and peptide library workflows to introduce a 4-pyridyl side chain at defined positions, enabling heteroaromatic-rich sequences for structure-function studies. Peptide chemists commonly select this amino acid when they want a side chain that can act as a coordination site or a directional interaction element in binding assays, without relying on post-synthetic modification. In practice, it supports the preparation of sequence-defined peptides for receptor/ligand interaction mapping, conformational studies, and comparative SAR-style experiments where the pyridine nitrogen provides a consistent electronic and hydrogen-bonding motif.
2. Metal Coordination Ligands
3-(4-Pyridyl)-L-Alanine is frequently incorporated into ligand design for coordination chemistry applications, including the preparation of amino-acid-derived chelators and metal-binding scaffolds used in chemical biology and materials research. The 4-pyridyl group offers a well-defined nitrogen donor that can coordinate with transition metals, supporting studies of metal-peptide interactions, controlled complexation behavior, and metal-dependent assembly. Teams developing coordination-driven supramolecular systems, metal-responsive materials, or metal-binding reference compounds rely on this amino acid to provide a chiral, amino-acid-derived backbone while maintaining the pyridine coordination site in a predictable orientation.
3. Pharmaceutical Intermediate Development
3-(4-Pyridyl)-L-Alanine is used as a chiral intermediate in medicinal chemistry and pharmaceutical intermediate development programs that require a heteroaromatic amino-acid motif. Synthetic teams value the defined L-stereochemistry and the pyridine side chain as a stable functional element that can be carried through downstream transformations to generate amino-acid-containing fragments, heteroaryl-substituted scaffolds, or protected derivatives used in larger coupling sequences. This amino acid is also selected when a pyridine nitrogen must remain available for later derivatization or for final compound properties such as basicity and hydrogen-bond acceptor capability.
4. Analytical Reference Synthesis
3-(4-Pyridyl)-L-Alanine is applied in analytical chemistry workflows where a structurally defined amino acid standard or calibration component is needed, particularly for methods targeting amino-acid-like heteroaromatic analytes. Analytical teams use it to support method development and validation for chromatography and mass spectrometry-based quantification of pyridyl-containing amino acid derivatives, including studies where the pyridine side chain provides a distinctive analytical signature. In metabolite profiling and targeted quantitation contexts, it can serve as a reference material to confirm retention behavior and mass spectral features for related compounds generated during derivatization or sample processing.
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