3-(2-Pyridyl)-D-alanine is a D-configured amino acid derivative in which the side chain bears a 2-pyridyl (pyridine) heteroaromatic ring. The molecule contains a free amino group and a carboxyl group characteristic of amino acid building blocks, with the pyridyl nitrogen providing a basic heteroatom that can participate in coordination and hydrogen-bonding interactions. In research and synthetic chemistry contexts, it is used as a chemically defined amino acid analogue for preparing peptides and peptide conjugates that incorporate a pyridine-containing side chain for structure-activity studies, metal-binding or coordination-controlled assays, and analytical method development.
CAT No: CP22802
CAS No:37535-52-7
Synonyms/Alias:3-(2-Pyridyl)-D-alanine;37535-52-7;(R)-2-Amino-3-(pyridin-2-yl)propanoicacid;(R)-2-Pyridylalanine;2'-Aza-D-phenylalanine;2-PYRIDYL-D-ALA;(2R)-2-amino-3-(pyridin-2-yl)propanoicacid;D-2-PYRIDYLALANINE;2'-PYRIDYL-D-ALA;D-3-(2-pyridyl)-alanine;(2R)-2-amino-3-(2-pyridyl)propanoicacid;3-(2-PYRIDYL)-D-ALA-OH;SBB065302;(R)-2-Amino-3-(2-pyridyl)propionicacid;2-Aza-D-phenylalanine;3-(Pyridin-2-yl)-D-alanine;2-[(2R)-2-Amino-2-carboxyethyl]pyridine;PubChem5694;3-pyridin-2-yl-D-alanine;3-(2-Pyridinyl)-D-alanine;95718_ALDRICH;SCHEMBL243557;3-(Pyridin-2-yl)-L-alanine;H-D-ALA(2-PYRI)-OH;D-ALA(2'-PYRIDYL)-OH
3-(2-Pyridyl)-D-alanine is a D-configured alanine analog bearing a 2-pyridyl substituent on the side chain, providing a heteroaromatic nitrogen that can participate in coordination chemistry and specific recognition in chemical biology workflows. This amino acid building block is commonly used when a stereochemically defined alanine mimic is needed alongside a pyridyl handle for metal binding, ligand design, or structure-guided labeling strategies. Its compact, amino-acid-like framework makes it practical for incorporation into synthetic sequences and for use as a defined reagent in analytical and materials-related studies.
1. Peptidomimetic Building Block
3-(2-Pyridyl)-D-alanine is used as a stereodefined alanine mimic in peptidomimetic and peptide analog synthesis, where the D-configuration and pyridyl side chain help control local geometry and introduce a directional heteroaromatic functionality. Medicinal chemistry groups and peptide-material developers employ this building block to prepare short analogs for structure-activity relationship studies, conformational probing, and binding-site mapping, particularly when a pyridyl nitrogen is required as a coordination site or as a polar interaction element. Because the molecule retains an amino-acid backbone, it can be integrated into custom peptide synthesis workflows to generate well-defined analogs for downstream characterization.
2. Metal Coordination Ligand Design
3-(2-Pyridyl)-D-alanine is frequently selected for ligand construction in coordination chemistry and chemical biology tool development, leveraging the 2-pyridyl nitrogen as a site for metal binding. Researchers in materials chemistry and bioinorganic chemistry use this amino acid analog to build defined metal-ligand motifs for studying coordination behavior, tuning stability of metal complexes, and creating reproducible binding environments for analytical assays. The D-alanine stereocenter can be advantageous when a chiral or stereochemically biased ligand scaffold is needed to influence complex formation and to provide consistent performance across comparative experiments.
3. Analytical Reference And LC-MS Tracing
3-(2-Pyridyl)-D-alanine is used as a defined analytical standard and reference reagent in method development and quantitative workflows that require a structurally specific amino acid analog. Analytical chemistry laboratories incorporate this compound into calibration strategies for LC-MS or related chromatographic platforms when monitoring pyridyl-containing amino acid species, verifying derivatization performance, or benchmarking retention and ionization behavior for structurally related analytes. Its clear heteroaromatic signature and amino-acid framework make it a practical choice for instrument qualification and for supporting reproducible identification in complex sample matrices used in research settings.
4. Biomolecule Labeling Probes
3-(2-Pyridyl)-D-alanine supports chemical biology probe development where a pyridyl-containing amino acid motif is used to introduce a defined recognition element or a metal-coordination handle for secondary detection strategies. Chemical biology groups use this building block to construct probes or probe precursors that can be incorporated into larger labeling reagents, enabling controlled presentation of a heteroaromatic functionality while maintaining an amino-acid-like scaffold for conjugation planning. In downstream workflows, the pyridyl group can serve as a functional anchor for assembling probe architectures that are compatible with analytical readouts and structured interaction studies.
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