3-(3- Pyrrolidinyl)-D-alanine is a non-proteinogenic, D-configured amino acid derivative featuring an alanine backbone substituted at the 3-position with a pyrrolidinyl side chain. The molecule contains a free amino group and a free carboxyl group on the amino acid framework, while the appended pyrrolidine ring provides a secondary amine functionality that can participate in acid-base equilibria and nucleophilic interactions during chemical synthesis. This amino acid analogue is used in peptide chemistry and structure-activity studies to introduce a conformationally constrained, basic side-chain element into amino acid sequences or to serve as a defined building block for preparing more complex amino acid and peptide derivatives.
CAT No: CP23302
3-(3- Pyrrolidinyl)-D-alanine is a D-configured amino acid derivative featuring a side chain substituted with a pyrrolidinyl group, providing a basic, conformationally constrained functionality that is often leveraged in medicinal chemistry and peptide-related scaffold design. Its amino acid backbone supports incorporation into synthetic sequences or chemical ligation strategies, while the pyrrolidine substituent offers a handle for tuning polarity, hydrogen-bonding patterns, and local steric environment. As a non-proteinogenic building block, it is commonly used to probe structure-activity relationships and to prepare defined stereochemical intermediates for downstream synthesis.
1. Peptidomimetic Building Block
3-(3- Pyrrolidinyl)-D-alanine is used by medicinal chemistry and chemical biology teams to construct peptidomimetic analogs where a D-amino acid stereocenter and a basic pyrrolidinyl side chain help define three-dimensional shape and intermolecular interaction profiles. Researchers incorporate this building block into short peptides, constrained peptidomimetics, and SAR libraries to systematically evaluate how side-chain protonation and steric bulk influence binding-site engagement and overall molecular recognition. Because the compound is supplied as a defined stereochemical unit, it supports reproducible library synthesis and consistent structure definition across analog series.
2. Stereodefined SAR Intermediates
3-(3- Pyrrolidinyl)-D-alanine serves as a stereodefined intermediate for preparing analogs used in structure-activity relationship studies and conformational tuning campaigns. Medicinal chemistry groups frequently select D-amino acid derivatives like this one to control backbone orientation and to introduce non-proteinogenic character into lead optimization workflows. The pyrrolidinyl substituent provides a practical means to adjust basicity and hydrogen-bonding capacity without changing the core amino acid framework, enabling targeted exploration of how side-chain electronics and geometry affect downstream synthetic targets.
3. Chemical Biology Probe Synthesis
3-(3- Pyrrolidinyl)-D-alanine is applied in chemical biology workflows that require defined, non-natural amino acid components for probe construction and binding studies in assay development. Teams designing receptor ligands, substrate analogs, or interaction-mapping reagents often use D-configured, pyrrolidinyl-bearing amino acids to create probes with controlled stereochemistry and a basic side chain that can participate in specific noncovalent interactions. In these workflows, the compound functions as a modular building block that can be incorporated into larger probe scaffolds during custom synthesis, supporting consistent probe structure across experimental batches.
4. Pharmaceutical Intermediate Development
3-(3- Pyrrolidinyl)-D-alanine is also used as a specialty intermediate in pharmaceutical intermediate development where defined stereochemistry and side-chain functionality are required for scalable synthesis of advanced building blocks. Process and development chemists rely on such amino acid derivatives to assemble more complex heteroatom-rich fragments while maintaining the stereochemical integrity of the D-center. The pyrrolidinyl group can be retained through intermediate stages to preserve key physicochemical properties in later coupling or diversification steps, making the compound useful for downstream manufacturing of research and development candidates.
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