N-α-Fmoc-N-γ-1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)ethyl-L-2,4-diaminobutyric acid is an Fmoc-protected, L-configured amino acid derivative belonging to the diaminobutyric acid class, bearing an N-α Fmoc group and an N-γ substituted side chain. The molecule contains an Fmoc carbamate at the amino terminus, a free carboxyl functional group, and a substituted amino-bearing side chain that incorporates a 4,4-dimethyl-2,6-dioxocyclohex-1-ylidene (cyclohexanedione-derived) moiety, providing a conjugated, electrophile-like carbonyl environment while maintaining the stereochemical designation indicated by the "L" label. In peptide and amino-acid derivative synthesis, the N-α Fmoc protection supports stepwise assembly on solid or solution-phase platforms, while the cyclohexanedione-derived N-substitution and the 2,4-diaminobutyric backbone provide a chemically defined handle for incorporating a functionalized diamino acid residue into larger peptide constructs or for preparing structured conjugation and structure-activity study materials.
CAT No: CP05326
N-α-Fmoc-N-γ-1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)ethyl-L-2,4-diaminobutyric acid is an Fmoc-protected, chiral amino acid derivative featuring an L-2,4-diaminobutyric acid core with orthogonally addressable amino functionality and a strongly electron-withdrawing, cyclic imide-like carbonyl system appended through an N-γ substituted ylidene/ketone motif. The molecule contains a fluorenylmethoxycarbonyl (Fmoc) group on the α-nitrogen for base-labile protection during peptide assembly, alongside additional protected/activated nitrogen character that can be leveraged for selective coupling and subsequent unveiling of reactive amines. Multiple carbonyl groups within the appended cyclohexane-2,6-dione framework provide defined polarity and can participate in controlled derivatization, while the stereogenic center supports stereochemically consistent incorporation into peptide sequences. The resulting protected amino acid building block functions as a chemically stable intermediate for peptide synthesis and for constructing side-chain modified residues that carry a carbonyl-rich, conformationally informative substituent into downstream targets.
1. Peptide Synthesis
N-α-Fmoc-N-γ-1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)ethyl-L-2,4-diaminobutyric acid is suited to solid-phase peptide synthesis workflows where Fmoc protection on the α-amine supports iterative N-to-C coupling cycles. The presence of an L-2,4-diaminobutyric acid scaffold enables incorporation of a diamino side-chain residue, and the N-γ substituted, carbonyl-rich ylidene motif can be used to control chemoselectivity by temporarily masking or modulating nucleophilicity of the additional amine(s). The appended diketone/activated carbonyl system can remain intact through peptide assembly conditions, allowing later on-resin or solution-phase transformations to generate functionalized peptide analogs. Downstream, the residue can be used to build peptidic scaffolds with defined side-chain polarity and potential intramolecular interactions, supporting structure-driven peptide design and synthetic library generation.
2. Amino Acid Derivatization
N-α-Fmoc-N-γ-1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)ethyl-L-2,4-diaminobutyric acid supports amino acid derivatization strategies that exploit orthogonal nitrogen handling and carbonyl-rich substituent chemistry. The Fmoc group enables controlled deprotection to reveal the α-amine for coupling or for forming new amide/urea linkages, while the additional amino functionality on the 2,4-diaminobutyric acid core can be addressed through selective protection/deprotection sequences compatible with peptide-grade reagents. The 4,4-dimethyl-2,6-dioxocyclohex-1-ylidene motif introduces multiple carbonyl acceptors that can participate in further functional group transformations, including nucleophile-mediated modifications after liberation of the relevant nitrogen sites. The resulting derivatives can serve as biochemical research intermediates, chiral building blocks for fine chemical synthesis, and tunable side-chain platforms for generating amino acid conjugates and peptidomimetic fragments.
3. Bioconjugation Chemistry
N-α-Fmoc-N-γ-1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)ethyl-L-2,4-diaminobutyric acid can be applied to bioconjugation workflows that require amino acid-derived handles for controlled coupling to biomolecules. The diamino nature of the L-2,4-diaminobutyric acid backbone provides multiple nitrogen sites that can be selectively exposed or transformed into reactive amide, urea, or other nitrogen-containing linkages after Fmoc removal and appropriate orthogonal protection management. The carbonyl-rich cyclohexanedione/ylidene substituent contributes defined polarity and can influence conjugate solubility and binding behavior in chemical biology experiments. Downstream conjugates may be prepared as stable peptide-based linkers, labeling reagents, or modular fragments for attaching to proteins or nucleic-acid-associated scaffolds, supporting molecular recognition studies and analytical method development.
4. Peptidomimetics And SAR Studies
N-α-Fmoc-N-γ-1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)ethyl-L-2,4-diaminobutyric acid is relevant to peptidomimetic construction and structure-activity relationship studies where side-chain electronics and stereochemistry must be encoded into a defined residue. The L stereocenter ensures stereochemical consistency when the residue is incorporated into analogs, while the diamino side-chain can be used to tune hydrogen-bonding patterns and charge distribution across a peptide-like framework. The appended 2,6-dioxocyclohexylidene motif introduces a rigid, carbonyl-dense element that can modulate conformational preferences and create specific interaction motifs with target binding pockets. Synthetic incorporation of this residue enables systematic SAR exploration by generating analog series in which the side-chain substitution pattern is varied while maintaining a consistent backbone geometry and coupling-ready functional group architecture.
5. Pharmaceutical Manufacturing Intermediates
N-α-Fmoc-N-γ-1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)ethyl-L-2,4-diaminobutyric acid can serve as a process chemistry intermediate for manufacturing peptide building blocks used in industrial peptide and peptidomimetic production. The Fmoc-protected α-amine supports standard peptide coupling compatibility, and the chemically robust carbonyl-rich substituent is designed to withstand common peptide assembly conditions without uncontrolled side reactions. The presence of multiple nitrogen sites enables downstream conversion into defined amide or urea functionalities, facilitating controlled specification of intermediate identity in multi-step synthesis routes. Industrially, the compound can be employed to prepare residue-containing intermediates for scale-up synthesis of protected amino acid derivatives and peptide analogs, supporting reproducible manufacturing of complex, side-chain functionalized products.
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