Boc-D-Piperidine-2-carboxylic acid is a protected, non-proteinogenic amino acid derivative featuring a piperidine ring bearing a carboxylic acid at the 2-position and a Boc-protected amino function, with the D stereochemical designation indicated in the name. The molecule contains a tert-butoxycarbonyl (Boc) carbamate that masks the α-amino group while presenting a free carboxylic acid for coupling chemistry, and its cyclic secondary amine framework provides a conformationally constrained side-chain environment. It is used as a precursor in peptide and peptidomimetic synthesis to introduce a D-configured piperidine-containing residue, supporting stepwise assembly and chemoselective amide-bond formation through the orthogonally protected functional groups.
CAT No: CP22504
CAS No:28697-17-8
Synonyms/Alias:28697-17-8;(R)-(+)-N-Boc-2-piperidinecarboxylicacid;(R)-1-(tert-butoxycarbonyl)piperidine-2-carboxylicacid;BOC-D-PIPECOLICACID;(D)-N-Boc-Pipecolicacid;(R)-N-Boc-piperidine-2-carboxylicacid;(R)-1-Boc-Piperidine-2-carboxylicacid;Boc-D-Pip-OH;(R)-1-N-Boc-Pipecolinicacid;(+)-N-Boc-(R)-pipecolinicacid;(r)-n-boc-pipecolicacid;MFCD00237380;2(R)-1-(tert-Butoxycarbonyl)piperidinecarboxylicacid;N-Boc-D-pipecolicacid;Boc-(R)-(+)-piperidine-2-carboxylicacid;(2R)-1-(tert-butoxycarbonyl)piperidine-2-carboxylicacid;(2R)-1-[(tert-butoxy)carbonyl]piperidine-2-carboxylicacid;(R)-(+)-1-(tert-Butoxycarbonyl)-2-piperidinecarboxylicacid;Maybridge4_003680;L-Pipecolinicacid,N-BOCprotected;boc-d-hopro-oh;boc-d-homopro-oh;boc-d-homoproline;PubChem5636;PubChem5735
Boc-D-Piperidine-2-carboxylic acid is a D-configured, Boc-protected piperidine-2-carboxylic acid building block used to introduce a rigid cyclic amino acid motif into peptides and peptidomimetics. The Boc protecting group provides a protected amino functionality for controlled coupling strategies, while the carboxylic acid enables downstream activation and incorporation into amide linkages. This scaffold is frequently selected in medicinal chemistry and peptide engineering workflows where conformational constraint and stereochemical definition are important for structure-activity relationship studies.
1. Peptidomimetic Building Blocks
Boc-D-Piperidine-2-carboxylic acid is used as a protected cyclic amino acid building block for assembling peptidomimetics and constrained peptide analogs in solution-phase or automated peptide synthesis workflows. Researchers in medicinal chemistry and chemical biology select this D-piperidine scaffold to emulate stereodefined backbone geometry and to probe how ring-constrained side-chain presentation affects binding, conformation, and overall molecular shape. The Boc-protected amino group supports stepwise construction of amide bonds, enabling incorporation of the cyclic residue at defined positions during custom synthesis of analog series.
2. Solid-Phase Peptide Synthesis
Boc-D-Piperidine-2-carboxylic acid is commonly employed in workflows that require a protected amino acid residue for stepwise peptide chain assembly, including library synthesis where cyclic constraints are introduced systematically. Peptide synthesis groups use this building block to generate sequences containing a piperidine-2-carboxylate-derived residue, supporting structure-activity relationship campaigns that compare linear versus conformationally restricted analogs. The presence of the Boc-protected nitrogen helps maintain controlled reactivity during iterative coupling and deprotection cycles, facilitating reproducible incorporation of the D-configured cyclic unit into longer peptide constructs.
3. Pharmaceutical Intermediate Development
Boc-D-Piperidine-2-carboxylic acid is also used as a pharmaceutical intermediate building block for manufacturing research intermediates that contain a D-piperidine-2-carboxylic acid motif. Process development chemists and intermediate manufacturers rely on this protected form to manage functional-group compatibility during multistep synthesis, particularly when the cyclic amino acid core must be carried through upstream transformations before final coupling or derivatization. This makes the reagent relevant to the preparation of advanced intermediates used in the synthesis of peptide-like small molecules and other conformationally constrained scaffolds.
4. Chiral Structure-Activity Studies
Boc-D-Piperidine-2-carboxylic acid supports chiral SAR development by providing a stereochemically defined D-configured cyclic amino acid unit for comparative studies against other stereoisomers or alternative side-chain architectures. Medicinal chemistry teams use this building block to systematically vary stereochemistry and conformational constraints within peptide-derived scaffolds, helping clarify how stereochemical inversion and ring constraint influence physicochemical properties and structure-dependent behavior in chemical biology assays. The rigid piperidine framework provides a practical handle for designing analog panels where stereochemical effects are decoupled from more flexible side-chain changes.
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