3-(3- Pyrrolidinyl)-DL-alanine is a DL (racemic) alanine derivative in which the side chain bears a 3-pyrrolidinyl substituent, making it a non-proteinogenic, structurally modified amino acid suitable for peptide and chemical biology studies. The molecule contains both an amino group and a carboxyl group on the alanine backbone, while the pyrrolidinyl moiety provides a secondary amine that can participate in acid-base equilibria and serve as a reactive functional handle for conjugation or derivatization. As a substituted amino acid, it is used as a building block for preparing peptide analogues and other amino acid derivatives that probe structure-activity relationships, introduce cationic or amine-containing features into synthetic sequences, or support analytical labeling strategies.
CAT No: CP23303
3-(3- Pyrrolidinyl)-DL-alanine is a DL-configured alanine derivative bearing a pendant pyrrolidine side chain, providing a basic, amine-containing functionality that is useful for medicinal chemistry and structure-activity relationship work. As a non-proteinogenic amino acid building block, it is typically handled as a stereoracemate, enabling parallel synthesis and library generation where side-chain identity and basicity are key variables. Its amino-bearing side chain also makes it a practical precursor for further derivatization into amide, urea, or salt forms used in downstream coupling and analytical workflows.
1. Peptidomimetic Building Block
3-(3- Pyrrolidinyl)-DL-alanine is used as a non-natural amino acid building block for constructing peptidomimetics and constrained analogs where a pyrrolidine-containing side chain is required to tune sterics and basicity. Medicinal chemistry groups incorporate this residue into short peptide-like scaffolds during lead optimization to probe how side-chain nitrogen identity and spatial presentation affect target engagement and physicochemical properties. Because the material is supplied as a DL stereoracemate, it is commonly selected for early-stage SAR campaigns and parallel synthesis, where rapid access to side-chain functionality is prioritized over single-enantiomer stereocontrol.
2. Pharmaceutical Intermediate Derivatization
3-(3- Pyrrolidinyl)-DL-alanine is frequently employed as a versatile intermediate for preparing downstream nitrogen-containing derivatives used in pharmaceutical intermediate development. The presence of both amino functionality and an amino-acid backbone enables conversion into protected or activated forms that can be carried forward into coupling steps for heterocycle-containing fragments, amide-forming intermediates, and salt preparations for process development. Process chemists and custom synthesis teams value this building block when the pyrrolidine side chain must be introduced early into a synthetic sequence, allowing consistent handling of a defined nitrogen motif across multiple candidate structures.
3. SAR Library Synthesis
3-(3- Pyrrolidinyl)-DL-alanine supports combinatorial and analog synthesis workflows aimed at mapping structure-activity relationships for basic side-chain motifs. Chemical biology and medicinal chemistry laboratories use this residue to generate series of analogs that vary the attachment point, oxidation state, or N-substitution pattern of the pyrrolidine nitrogen through subsequent derivatization steps. The DL format is particularly useful for building diverse libraries quickly, enabling researchers to evaluate trends across stereochemical mixtures before committing to enantioenriched follow-up targets.
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