4-Amino-piperidine-4-carboxylic acid is a cyclic, non-proteinogenic amino acid featuring a piperidine ring bearing a carboxylic acid at the 4-position and a primary amino group also at the 4-position. The molecule contains both amino and carboxyl functional groups on the same ring carbon framework, which constrains the side-chain geometry relative to open-chain amino acids and supports defined conformational behavior during derivatization or coupling. In synthesis and chemical biology workflows, it is employed as a building block for preparing constrained amino acid and peptide analogues, as well as for structure-activity studies and analytical method development where a ring-constrained amino acid scaffold is required.
CAT No: CP27096
CAS No:40951-39-1
Synonyms/Alias:4-Aminopiperidine-4-carboxylicacid;40951-39-1;4-AMINO-4-PIPERIDINECARBOXYLICACID;4-Amino-piperidine-4-carboxylicacid;PubChem4003;4-AminonipecoticAcid;AC1LTTA9;SCHEMBL180209;CTK1D8705;KHABBYNLBYZCKP-UHFFFAOYSA-N;MolPort-000-000-386;ANW-59934;ZINC21298884;4-Piperidinecarboxylicacid,4-amino-;AKOS007930608;PB12229;AJ-78224;AK-30003;AM010435;KB-72070;SC-04350;AB0081637;AB1006470;TL8002217;FT-0617422
4-Amino-piperidine-4-carboxylic acid is a cyclic, conformationally constrained amino acid building block featuring a piperidine ring with a primary amino group and a carboxylic acid at the 4-position. This structure makes it a practical scaffold for medicinal chemistry and peptidomimetic design, where ring constraint can influence three-dimensional shape and synthetic tractability. Researchers commonly use this compound as a defined chiral or achiral amino acid-like unit for assembling amide-containing motifs and for preparing intermediates that feed into larger heterocycle- and peptide-like systems.
1. Peptidomimetic Building Block
4-Amino-piperidine-4-carboxylic acid is used to construct constrained peptidomimetics and amide-linked scaffolds in small-molecule and peptide-drug-discovery programs. Medicinal chemistry groups value the piperidine ring for providing a rigidified geometry around the amino acid-like center, enabling analog libraries where stereochemical and conformational effects are explored systematically. The presence of both a primary amino group and a carboxylic acid supports downstream derivatization into amide and urea-like linkages, which are frequently encountered in SAR workflows. This compound is typically handled as a research-grade building block for solution-phase synthesis of constrained fragments and for preparing defined intermediates for larger coupling sequences.
2. Pharmaceutical Intermediate Synthesis
4-Amino-piperidine-4-carboxylic acid serves as a versatile intermediate for manufacturing-defined heterocycle-containing structures used in pharmaceutical intermediate development. Process and synthetic chemistry teams incorporate this amino acid-like unit into routes that require a stable, isolable scaffold bearing two orthogonally addressable functional handles (carboxyl functionality and a primary amine). That dual functionality supports conversion into activated carboxy derivatives for coupling, as well as transformation of the amine into protected or substituted forms to enable sequential assembly of complex molecules. The cyclic backbone also helps reduce conformational heterogeneity in the resulting intermediates, which can simplify characterization and support reproducible downstream transformations.
3. Heterocycle-Ligand Derivatization
4-Amino-piperidine-4-carboxylic acid is frequently employed to generate ligand-like fragments and nitrogen-rich binding motifs for chemical biology and receptor-binding chemistry. The piperidine ring and primary amine provide a foundation for introducing substituents that modulate basicity, hydrogen-bonding capacity, and overall scaffold topology—properties that are central to designing small-molecule probes and binding partners. Synthetic chemists use the carboxylic acid handle to create amide-linked attachment points, while the amino group enables further functionalization to tune solubility and interaction patterns within a series. In practice, the compound is used to prepare defined analogs that can be carried forward into larger conjugation or screening libraries.
4. Analytical Reference Material
4-Amino-piperidine-4-carboxylic acid is also used as a structural reference and calibration component in analytical method development for amino acid-like and heterocyclic amine-containing compounds. Analytical chemistry laboratories rely on such well-defined standards to verify retention behavior, confirm derivatization outcomes, and support method qualification for LC-based workflows that target carboxylic acids and primary amines. Because the compound contains both key functional groups that respond to common derivatization and detection strategies, it can serve as a practical benchmark for monitoring reaction mixtures and for validating quantitative performance in assays that include constrained amino acid motifs.
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