(RS)-3-Amino-3-(3-pyridyl)-propionic acid is a non-proteinogenic amino acid featuring a three-carbon backbone bearing an amino group at the 3-position and a 3-pyridyl substituent on the same carbon, classifying it as a pyridyl-substituted amino acid derivative. The molecule contains a free primary amino group and a free carboxylic acid, and the (RS) designation indicates a racemic mixture at the stereogenic center created by the substituted 3-position. As a chemically defined building block, it is used in peptide and peptidomimetic synthesis and in structure-activity or chemical biology studies where the pyridine ring provides a nitrogen-containing aromatic handle for coordination, conjugation, or analytical derivatization.
CAT No: CP27282
CAS No:62247-21-6
Synonyms/Alias:Z-Dab-OH;62234-40-6;Z-Dbu-OH;Cbz-L-2,4-diaminobutyricacid;N-alpha-Cbz-L-2,4-diamiobutyricacid;(S)-4-amino-2-(benzyloxycarbonylamino)butanoicacid;(S)-4-Amino-2-(((benzyloxy)carbonyl)amino)butanoicacid;Nalpha-Z-L-2,4-diaminobutyricacid;(2S)-4-amino-2-{[(benzyloxy)carbonyl]amino}butanoicacid;(2S)-4-AMINO-2-[[(BENZYLOXY)CARBONYL]AMINO]BUTANOICACID;N-A-Z-D-2,4-DIAMINOBUTYRICACID;PubChem13825;Z-DAB;Z-L-DAB-OH;96083_ALDRICH;SCHEMBL1023794;96083_FLUKA;EBD4602;KXMSCBRTBLPGIN-JTQLQIEISA-N;MolPort-003-939-925;ACT04328;N|A-Z-L-2,4-diaminobutyricacid;ZINC2555266;FD1079;KM0591
(RS)-3-Amino-3-(3-pyridyl)-propionic acid is a non-proteinogenic, side-chain-functional amino acid featuring a pyridine ring at the β-position relative to the amino group, providing a basic heteroaromatic handle for coordination chemistry and medicinal chemistry workflows. Presented as the racemic (RS) mixture, it is commonly used as a chiral building block precursor in structure-activity relationship studies and in the preparation of heteroaryl-containing peptide and peptidomimetic scaffolds. The amino acid functionality supports downstream derivatization into protected intermediates and coupling-ready forms for synthetic campaigns where heteroaryl incorporation is required.
1. Peptidomimetic Building Block
(RS)-3-Amino-3-(3-pyridyl)-propionic acid is used by medicinal chemistry and chemical biology groups to introduce a pyridyl-bearing amino acid motif into peptidomimetic structures and constrained analogs. Its heteroaromatic side chain is frequently leveraged to tune physicochemical properties and enable specific noncovalent interactions in SAR libraries, while the amino acid backbone supports standard coupling strategies for assembling modified peptides or peptide-like scaffolds. The racemic (RS) form is often selected for early-stage library synthesis and intermediate generation, where stereochemical resolution can be deferred until later optimization steps.
2. Heteroaryl-Containing Intermediate Synthesis
(RS)-3-Amino-3-(3-pyridyl)-propionic acid serves as a practical starting material for producing downstream pharmaceutical intermediates that require a pyridine-functionalized carbon skeleton with an amino acid-derived functionality. Process and synthesis teams use it to generate protected amino acid derivatives and subsequent coupling partners for constructing larger heteroaryl-containing molecules, including kinase inhibitor fragments, receptor-binding motifs, and other N-heteroaryl scaffolds where a pyridine ring is central to binding or tuning electronic character. The presence of both an amino group and a basic pyridine provides a chemically informative platform for iterative derivatization during route development.
3. Coordination Chemistry Ligand Precursor
(RS)-3-Amino-3-(3-pyridyl)-propionic acid is applied in materials chemistry and analytical chemistry contexts as a ligand precursor for metal coordination studies and heteroaryl-containing chelating frameworks. The pyridine ring offers a straightforward nitrogen donor site, while the amino acid backbone can be transformed into derivatives that present additional donor functionality or provide controlled steric/electronic environments around the coordination center. Researchers often use this amino acid to build coordination complexes, to prepare functionalized ligands for surface or polymer attachment, or to support studies where metal-ligand interactions are probed using well-defined heteroaryl-containing building blocks.
4. Analytical Reference Derivatization
(RS)-3-Amino-3-(3-pyridyl)-propionic acid is also used for analytical method development and reference material preparation in workflows that require a defined pyridyl-amino acid motif. Analytical chemists may derivatize the amino acid to create standards for LC-MS or related quantitation approaches, particularly when monitoring synthetic intermediates, reaction mixtures, or degradation products that contain a pyridine-substituted amino acid structure. The racemic composition is advantageous when the analytical target is the total compound signal rather than enantiomer-specific quantification, supporting robust calibration and identification in routine analytical campaigns.
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