Boc-D-Lys(nicotinoyl)-OH is a Boc-protected derivative of D-lysine bearing a nicotinoyl acyl group on the lysine side-chain, placing it in the class of protected amino acid building blocks for peptide chemistry. The molecule contains a Boc carbamate on the α-amino group and a free carboxylic acid at the α-position, while the ε-amino side chain is converted to an amide through nicotinoylation, providing a stabilized, non-cationic side-chain functionality for controlled incorporation. In synthesis, this protected analogue is used as a stepwise amino acid reagent in peptide assembly where orthogonal protection and side-chain acylation help manage chemoselectivity and define the lysine-derived amide motif for structure-activity studies and derivative preparation.
CAT No: CP26257
CAS No:122546-52-5
Synonyms/Alias:Boc-D-Lys(nicotinoyl)-OH;122546-52-5;Boc-N-Epsilon-nicotinoyl-D-lysine;ZINC2555034;6340AH;I14-32682
Boc-D-Lys(nicotinoyl)-OH is a Boc-protected D-lysine derivative bearing a nicotinoyl-modified side chain, combining a protected amino acid backbone with an acylated, aromatic amide functionality. This structure is commonly handled as a peptide synthesis building block where the D-configuration and the side-chain nicotinoyl group provide stereochemical and functional differentiation for downstream assembly and structure-activity studies.
1. Stereodefined Peptide Building Block
Boc-D-Lys(nicotinoyl)-OH is used in custom peptide synthesis workflows to introduce a D-lysine residue with a side-chain nicotinoyl amide, enabling stereodefined sequence design for peptide libraries and SAR campaigns. Peptide chemists select this derivative when they need lysine-like spacing and charge patterning while simultaneously installing an aromatic amide functionality that can influence local conformation, hydrogen-bonding patterns, and physicochemical behavior of the resulting peptide. The Boc protection supports standard protected-amino-acid handling for segment coupling and iterative chain assembly, making it a practical choice for solution-phase or protected-residue peptide synthesis strategies where side-chain acylation is retained through assembly.
2. Peptidomimetic And SAR Studies
Boc-D-Lys(nicotinoyl)-OH serves as a targeted intermediate for peptidomimetic development, particularly when researchers want to compare analogs that differ at the lysine stereocenter and side-chain acyl substituent. Medicinal chemistry groups use this building block to generate peptide-like scaffolds with a defined D-lysine stereochemistry and an aromatic nicotinoyl group, supporting structure-activity relationship studies that probe how side-chain electronics and amide hydrogen-bonding capacity affect binding-mode hypotheses or functional readouts in chemical biology assays. Because the nicotinoyl group is already installed on the lysine side chain, it reduces variability associated with late-stage side-chain modifications and helps keep analog series chemically consistent across synthesis batches.
3. Aromatic Amide Functionalization In Peptides
Boc-D-Lys(nicotinoyl)-OH is applied when an aromatic nicotinamide motif within a peptide framework is required for downstream chemical biology workflows, including binding studies, receptor/ligand interaction mapping, and material-interaction investigations. Researchers incorporate this residue to position the nicotinoyl amide at a controlled location in the peptide sequence, leveraging the aromatic ring and amide functionality as a persistent chemical handle for subsequent derivatization strategies or for maintaining a specific interaction motif during assay development. In these applications, the Boc-protected backbone supports reliable incorporation as a discrete building block, while the pre-acylated side chain helps maintain the intended functionality without relying on post-assembly side-chain chemistry that can introduce heterogeneity.
4. Protected Intermediate For Analog Synthesis
Boc-D-Lys(nicotinoyl)-OH is also used as a protected amino acid intermediate for manufacturing-grade analog generation in research and development settings, where consistent reagent-to-reagent performance matters for multi-analog synthesis. Contract peptide manufacturers and academic peptide groups rely on such protected, side-chain-functionalized amino acids to streamline procurement of defined residues and to reduce the need for additional side-chain protection/deprotection steps during custom synthesis. This derivative is particularly valuable when the nicotinoyl-modified lysine side chain must remain intact through peptide assembly to deliver a uniform product profile for analytical characterization and comparative studies across peptide variants.
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