N-α-1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)ethyl-N-ε-allyoxycarbonyl-D-lysine is a D-lysine-derived amino acid derivative featuring a lysine backbone with an N-α substituted by a 4,4-dimethyl-2,6-dioxocyclohex-1-ylidene (cyclohexenone-like) group and an N-ε allyoxycarbonyl (Alloc) protecting group on the side-chain amine. The molecule retains the α-amino and α-carboxyl functionalities while the ε-amino group is masked as a carbamate, and the N-α substitution modifies the amide-forming reactivity relative to unprotected lysine while maintaining the stereochemical designation indicated by "D." As a protected, structurally modified lysine building block, it is used in peptide synthesis workflows where selective side-chain protection and controlled chemoselectivity are required, and the Alloc group provides a handle for orthogonal deprotection strategies during stepwise assembly of peptide derivatives.
CAT No: CP01429
N-α-1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)ethyl-N-ε-allyoxycarbonyl-D-lysine is a D-lysine derivative bearing an Nα-alkylidene protecting group and an Nε allyoxycarbonyl (Alloc) carbamate. The lysine backbone provides a stereogenic α-carbon and a side-chain ε-amino group that is masked as a removable carbonate, while the Nα functionality is protected in a way that supports controlled peptide coupling chemistry. The molecule contains two carbonyl-rich motifs, including the cyclohexenylidene-derived urea-like/activated carbonyl system and the carbamate carbonyl, which influence solubility, acylation behavior, and deprotection selectivity during protected amino acid synthesis. The allyoxycarbonyl group can be converted under orthogonal deprotection conditions, enabling stepwise access to the ε-amine for subsequent peptide bond formation, side-chain derivatization, or downstream intermediate construction.
1. Peptide Synthesis
N-α-1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)ethyl-N-ε-allyoxycarbonyl-D-lysine is used in peptide building workflows where orthogonal protection of the α-amino and ε-amino functions is required. The Nε Alloc carbamate allows selective unveiling of the lysine side-chain amine for lysine-internal coupling, branching, or late-stage functionalization, while the Nα protecting group supports controlled N-terminal activation and acylation. The presence of multiple carbonyl groups enables compatibility with standard peptide coupling strategies by stabilizing reactive intermediates and maintaining a protected amino acid form during chain assembly. The resulting lysine-containing peptide sequences and protected peptide fragments can be advanced into longer constructs for library synthesis, structure-activity relationship studies, and peptide analogue generation.
2. Side-Chain Functionalization
N-α-1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)ethyl-N-ε-allyoxycarbonyl-D-lysine supports side-chain functionalization strategies that rely on controlled access to the D-lysine ε-amine. The Alloc-protected ε-nitrogen can be unmasked to introduce amide, urea, sulfonamide, or other nitrogen-bearing linkages, enabling attachment of charged handles, affinity tags, or solubilizing moieties to lysine-rich scaffolds. The D-configuration at the α-carbon provides stereochemical control for unnatural amino acid incorporation into peptides and peptidomimetics, supporting investigations where stereochemistry affects conformation and binding. Downstream derivatives prepared from the deprotected ε-amine can serve as intermediates for conjugation chemistry and as modular units in synthetic organic chemistry.
3. Chemical Biology Labeling
N-α-1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)ethyl-N-ε-allyoxycarbonyl-D-lysine can be applied in chemical biology workflows that require lysine-directed conjugation handles under protected-amino-acid conditions. The lysine ε-amine, once revealed from the allyoxycarbonyl carbonate, can participate in amide-forming coupling to link fluorophores, biotin-like affinity groups, or reactive probes to peptide backbones. The Nα-protected state helps maintain chemoselectivity during multi-step synthesis, reducing undesired reactions during probe installation and enabling controlled generation of labeled peptides or peptidomimetic fragments. The stereodefined D-lysine residue supports the construction of labeling reagents used for biochemical assays, target engagement mapping, and molecular recognition studies where chirality and side-chain positioning matter.
4. Peptidomimetics And SAR Studies
N-α-1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)ethyl-N-ε-allyoxycarbonyl-D-lysine is suitable for peptidomimetic construction where lysine side-chain reactivity and stereochemical fidelity guide structure-activity relationship studies. The protected ε-amine enables systematic variation of side-chain substituents without perturbing the peptide coupling competence of the α-amino terminus, supporting iterative synthesis of analog series. D-lysine incorporation can be used to modulate backbone conformation and proteolytic stability in peptide analogs, while the orthogonal protection pattern supports late-stage diversification of the side chain. The resulting analogs can be used as research materials to correlate structural modifications with binding behavior and to generate SAR datasets across peptide-mimicking scaffolds.
5. Process Chemistry Intermediate
N-α-1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)ethyl-N-ε-allyoxycarbonyl-D-lysine can function as a manufacturing-oriented intermediate for producing protected lysine building blocks and downstream peptide fragments. The combination of an Nα-protected amino acid form and an Alloc-protected ε-amine provides a predictable protection/deprotection logic that can be integrated into scalable synthetic routes for fine chemical synthesis. Carbonyl-rich protecting groups support isolation as a defined protected intermediate while maintaining compatibility with peptide coupling and controlled deprotection steps used in industrial peptide manufacturing. The stereochemically defined D-lysine core enables consistent batch-to-batch construction of stereopure peptide intermediates used in specialty chemical production and applied biochemical reagent supply chains.
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