N-α-1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)ethyl-N-ε-Boc-L-lysine is a protected L-lysine derivative in which the ε-amino group is masked as a Boc carbamate and the α-amino/α-carboxyl region is incorporated into a substituted, cyclic carbonyl-containing "ylidene" framework. The molecule contains the lysine side chain terminating in a Boc-protected amine, while the α-position bears an additional carbonyl-rich ring substituent that modifies the balance of polarity and reactivity relative to free amino acids, and the stereochemistry is specified as L at the lysine center. In peptide and amino acid synthesis, this structure functions as a protected amino acid building block that can be used to control chemoselectivity during stepwise coupling while the Boc group and the modified α-substitution help regulate exposure of reactive nitrogen functionality and support preparation of further amino acid and peptide derivatives.
CAT No: CP01432
N-α-1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)ethyl-N-ε-Boc-L-lysine is an L-lysine derivative bearing an Nε-Boc-protected side-chain amine and an α-amino substituent that is linked to a 4,4-dimethyl-2,6-dioxocyclohex-1-ylidene (cyclohexenedione/activated enone-like) motif. The molecule contains the lysine backbone with a stereogenic α-center retained from L-lysine, while the appended electrophilic ring system introduces a carbonyl-rich, conjugated functionality that can participate in further derivatization or serve as a masked reactive handle. The presence of the Boc carbamate supports standard peptide-chemistry protection strategies for orthogonal deprotection, enabling selective exposure of the ε-amine when required. The combination of a protected amino acid framework and an additional carbonyl-bearing substituent makes the compound suitable as a chiral amino acid intermediate for peptide coupling chemistry, peptidomimetic construction, and downstream functional group installation.
1. Protected Amino Acid Synthesis
N-α-1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)ethyl-N-ε-Boc-L-lysine is applied in protected amino acid synthesis workflows where orthogonal protection and controlled functional-group exposure are required for stepwise assembly. The Nε-Boc group provides a stable carbamate protecting strategy for the lysine side-chain amine during peptide coupling or intermediate transformations, while the α-amino functionality remains positioned for incorporation into amide-forming steps. The appended 4,4-dimethyl-2,6-dioxocyclohex-1-ylidene motif introduces additional carbonyl functionality that can be carried through protection/deprotection sequences as a latent derivatization site. The resulting protected amino acid derivative can be used to prepare peptide building block preparations and chiral intermediates for fine chemical synthesis and process chemistry intermediate development.
2. Peptide Synthesis
N-α-1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)ethyl-N-ε-Boc-L-lysine is suited for peptide synthesis and peptide analog construction where lysine side-chain protection and selective coupling are central. The lysine backbone provides the canonical amino acid connectivity for forming amide bonds, while the Nε-Boc carbamate supports controlled handling of the ε-amine to prevent side reactions during N-terminus or backbone coupling. The α-substituted cyclohexenedione-like fragment can be retained as a functionalized residue that enables incorporation of a carbonyl-rich motif into peptide scaffolds for structure-activity relationship studies. The compound can therefore serve as a chiral, protected lysine-derived building block for generating functional peptide intermediates that support downstream derivatization and analytical characterization.
3. Side-Chain Functionalization
N-α-1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)ethyl-N-ε-Boc-L-lysine is used in side-chain functionalization and peptidomimetic design where lysine's ε-amine and the additional carbonyl-rich substituent enable targeted molecular modification. The Nε-Boc group allows ε-amine liberation under standard deprotection conditions, enabling conjugation chemistry, linker installation, or formation of additional amide/urea derivatives from the side-chain. The 4,4-dimethyl-2,6-dioxocyclohex-1-ylidene motif provides a conjugated, carbonyl-dense handle that can participate in further chemical transformations after incorporation or during intermediate elaboration. The resulting functionalized amino acid derivatives can be employed to generate libraries of modified lysine residues for biochemical research intermediate preparation, molecular scaffold diversification, and chemically defined probe construction.
4. Chemical Biology Probes
N-α-1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)ethyl-N-ε-Boc-L-lysine is applicable to chemical biology probe development and biomolecule modification strategies that require a protected, chiral amino acid precursor for controlled labeling. The protected lysine framework supports incorporation into peptide-based probes, while the orthogonal Boc protection strategy helps manage ε-amine reactivity during probe synthesis and subsequent conjugation steps. The carbonyl-rich α-substituent can function as a structural element that modulates polarity and hydrogen-bonding patterns, supporting defined interactions in peptide or peptidomimetic contexts used for target engagement studies. The compound can be converted into labeled or functionalized peptide constructs for use as chemical biology reagents, enabling downstream formation of well-defined biomolecule-modifying intermediates.
5. Process Chemistry Intermediate
N-α-1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)ethyl-N-ε-Boc-L-lysine is relevant to process chemistry and specialty chemical production as a chiral amino acid intermediate bearing a stable protecting-group strategy. The Boc-protected ε-amine reduces undesired side reactions during multistep manufacturing sequences, while the retained stereochemistry from L-lysine supports consistent chiral building block behavior across scale-up-oriented routes. The additional 4,4-dimethyl-2,6-dioxocyclohex-1-ylidene functionality provides a controllable functional handle that can be carried through manufacturing steps and later converted into downstream derivatives used in peptide science or fine chemical synthesis. The compound can therefore serve as a manufacturing intermediate for producing protected lysine derivatives and functionalized peptide building blocks used in industrial chemical manufacturing and applied research supply chains.
2. TMEM16F and dynamins control expansive plasma membrane reservoirs
3. SERS spectrum of the peptide thymosin‐β4 obtained with Ag nanorod substrate
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