N-α-Fmoc-N-ε-1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)-3-methylbutyl-D-lysine is a protected, derivatized lysine amino acid in which the α-amino group is capped with an Fmoc protecting group and the ε-amino side chain is substituted with an N-ε-1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene) moiety. The molecule contains a free carboxyl functional group and a D-lysine stereochemical configuration as indicated by the name, while its side chain bears the modified ε-amino functionality and a 3-methylbutyl substituent that changes the native lysine side-chain chemistry. As an amino-acid building block, it is used in peptide synthesis workflows to control chemoselectivity during stepwise assembly and to introduce a lysine-derived residue with a distinct, carbonyl-rich side-chain handle for subsequent chemical transformations or structure-property studies.
CAT No: CP01444
N-α-Fmoc-N-ε-1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)-3-methylbutyl-D-lysine is an Fmoc-protected D-lysine derivative bearing an Nε-alkylated side chain and a cyclic imide-type "ylidene" substituent that introduces two carbonyls within a constrained ring system. The molecule retains the stereogenic lysine backbone in the D configuration while presenting an Fmoc carbamate for orthogonal base-mediated deprotection during solid-phase peptide synthesis. The side-chain modification incorporates a bulky, carbonyl-rich functionality that can modulate polarity, hydrogen-bonding capacity, and amide/urea-forming reactivity under peptide-coupling conditions. The resulting protected amino acid building block behaves as a chiral, N-protected lysine analog suitable for controlled peptide coupling and downstream transformation into functionalized peptide scaffolds or synthetic intermediates.
1. Peptide Synthesis
N-α-Fmoc-N-ε-1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)-3-methylbutyl-D-lysine is used in peptide building workflows where Fmoc chemistry enables stepwise N-terminal protection and deprotection cycles. The Fmoc carbamate supports standard peptide coupling compatibility by presenting a protected α-amino group while the D-lysine stereocenter provides stereochemical control for lysine-containing sequences. The modified lysine side chain, featuring the carbonyl-rich cyclohexenylidene substituent, can be incorporated as a functionalized residue to introduce constrained polarity and altered intramolecular interactions within peptides. Downstream peptide analogs prepared from this residue can serve as tools for mapping backbone/side-chain recognition and for generating libraries of lysine variants for structure-guided design.
2. Amino Acid Derivatization
N-α-Fmoc-N-ε-1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)-3-methylbutyl-D-lysine is applied as a chiral amino acid intermediate for side-chain functionalization strategies that require a protected, stereodefined lysine scaffold. The Nε-substituent contains multiple carbonyl functionalities that can participate in further derivatization routes such as conversion to additional amide-like linkages or transformation into more reactive electrophiles under appropriate conditions. The protected α-amino group and Fmoc handle allow selective manipulation of the side-chain functionality without premature peptide coupling interference. The compound can thus serve as a precursor for generating functionalized lysine derivatives used in synthetic organic chemistry and biochemical reagent development.
3. Chemical Biology Probes
N-α-Fmoc-N-ε-1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)-3-methylbutyl-D-lysine is relevant to chemical biology research requiring D-amino acid-containing probes and lysine side-chain analogs with tuned hydrogen-bonding and steric profiles. The D configuration can be leveraged to probe stereospecific binding and protease resistance in peptide-like constructs, while the carbonyl-rich cyclohexenylidene substituent provides a defined polar motif for molecular recognition. Fmoc protection supports incorporation into longer peptide probes, enabling site-specific presentation of the modified lysine residue at a chosen position. Resulting labeled or functionalized peptide reagents can be used to interrogate binding interfaces, evaluate structure-activity relationships, and generate stereochemically controlled chemical tools.
4. Peptidomimetics And SAR Studies
N-α-Fmoc-N-ε-1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)-3-methylbutyl-D-lysine is suitable for peptidomimetic construction where lysine-like spacing and side-chain functionality are translated into constrained analogs. The modified side chain introduces a rigid, carbonyl-bearing group that can mimic or perturb interactions typically mediated by lysine's terminal amine, enabling systematic SAR studies across peptide scaffolds. The Fmoc-protected α-amino group permits incorporation into analog series using consistent coupling logic, while the D stereochemistry supports investigation of stereochemical effects on binding and conformational preferences. Downstream analogs derived from this residue can be used to build structure-focused series that relate side-chain polarity and steric constraints to molecular recognition outcomes.
5. Pharmaceutical Intermediate Preparation
N-α-Fmoc-N-ε-1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)-3-methylbutyl-D-lysine is employed in pharmaceutical intermediate preparation where protected amino acid building blocks feed into manufacturing routes for peptide-like active candidates and related fine chemicals. The Fmoc-protected α-amino functionality supports controlled deprotection and coupling logic in synthetic sequences, while the Nε-modified lysine side chain provides a defined functional handle for later conversion into final structural motifs. The presence of multiple carbonyl groups within the side-chain substituent can influence solubility and solid-state behavior of intermediates, which is relevant to downstream handling and purification planning. The compound can therefore function as a stereodefined, protected lysine-derived intermediate for producing functionalized peptide fragments and advanced intermediates used in applied chemical manufacturing.
6. Specialty Chemical Production
N-α-Fmoc-N-ε-1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)-3-methylbutyl-D-lysine is applicable to specialty chemical production that relies on chiral amino acid derivatives as feedstocks for functional materials and high-value reagents. The Fmoc group enables orthogonal protection management during synthesis, allowing the compound to be incorporated into larger conjugates or polymerizable/derivatizable fragments while maintaining stereochemical fidelity. The cyclohexenylidene carbonyl motif can serve as a polar, hydrogen-bonding element that modulates intermolecular interactions in the resulting materials or conjugates. The compound's structure supports its use as a chiral intermediate for generating functionalized lysine-based building blocks used in industrial fine chemical synthesis and applied materials chemistry.
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