N-α -1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)ethyl-D-2,3-diaminopropionic acid is a D-configured amino acid derivative featuring a 2,3-diaminopropionic acid backbone with an N-α substituted by a 1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)ethylidene moiety, classifying it as a structurally modified, nonstandard amino acid reagent rather than an unprotected natural amino acid. The molecule contains amino functional groups and a carboxylic acid, while the cyclic 2,6-dioxocyclohexylidene substituent introduces a constrained, carbonyl-bearing ring system that can alter nucleophilicity and overall chemoselectivity during peptide-related transformations. In synthesis and chemical biology workflows, this protected/derivatized amino acid analogue is used as a building block to control reactivity of the amino functionality and to introduce a defined, sterically constrained substituent for preparing substituted amino acid and peptide derivatives, as well as for analytical method development involving structurally characterized amino acid standards.
CAT No: CP05824
N-α -1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)ethyl-D-2,3-diaminopropionic acid is a D-configured amino acid derivative featuring a 2,3-diaminopropionic acid core with two stereochemically relevant amino functionalities and an α-substituted, ylidene-linked cyclohexanedione motif. The molecule bears a free carboxylic acid at the α-position while the side-chain amines can be engaged in protection/deprotection logic to control chemoselective peptide coupling and subsequent derivatization. The 4,4-dimethyl-2,6-dioxocyclohex-1-ylidene substituent introduces a rigid, electron-withdrawing carbonyl-rich scaffold that can influence solubility, reactivity, and conjugation chemistry while serving as a handle for downstream synthetic transformation. The overall structure functions as a chiral amino acid intermediate and a peptide-building block precursor where stereochemical integrity and functional-group orthogonality are central to constructing defined peptide analogs and amino acid derivatives.
1. Peptide Synthesis
N-α -1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)ethyl-D-2,3-diaminopropionic acid is suitable for peptide coupling workflows where the carboxylic acid and α-amino functionality participate in amide-bond formation using standard protected-amino-acid strategies. The D-2,3-diaminopropionic acid framework supports controlled N-terminal or side-chain incorporation by selecting orthogonal protecting groups for the two amines, enabling selective activation of the carboxyl group while maintaining chemoselective access to the desired nitrogen. The α-ylidene cyclohexanedione substituent can be retained through coupling steps and then used as a structural element in peptide analogs or for later functionalization, depending on the chosen protection scheme. Defined stereochemistry at the D-center supports the construction of stereochemically consistent peptide sequences and peptidomimetic scaffolds for structure-defined studies. This compatibility with protected amino acid chemistry makes the compound applicable to peptide building block preparation and downstream peptide analog synthesis.
2. Side-Chain Functionalization
N-α -1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)ethyl-D-2,3-diaminopropionic acid can be applied to amino acid derivatization programs that exploit its two amino groups and carbonyl-rich ylidene substituent for stepwise functional-group installation. The diamino side-chain enables selective derivatization toward urea, amide, sulfonamide, or heterocycle-forming intermediates after appropriate protection and activation of one amino site at a time. The cyclohexanedione-derived motif introduces electrophilic carbonyl functionality that can participate in condensation or scaffold elaboration routes, allowing the synthesis of rigidified analogs with altered polarity and hydrogen-bonding patterns. The free carboxylic acid supports conversion to activated esters or coupling-ready derivatives for attaching the amino acid to larger frameworks, including polymerizable handles. This structure therefore serves as a practical intermediate for generating functionalized amino acid derivatives and chemically defined building blocks for synthetic organic chemistry.
3. Chemical Biology Research
N-α -1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)ethyl-D-2,3-diaminopropionic acid is relevant to chemical biology workflows that require chiral, amino-acid-based probes for studying molecular recognition and protein-ligand interactions. The D-configured diamino acid core provides defined stereochemical information and multiple nitrogen sites that can be tuned for binding interactions, crosslinking chemistry, or incorporation into constrained peptide mimics. The carbonyl-rich cyclohexanedione ylidene substituent can function as a structural reporter element or as a platform for further derivatization into conjugatable motifs while maintaining the amino acid backbone for target engagement. Controlled protection of the amines supports selective labeling strategies, enabling preparation of single-site conjugates or defined analog libraries for biochemical assays. The compound's compatibility with peptide and amino acid modification chemistry supports its use as an intermediate toward probe construction and structure-driven biochemical research materials.
4. Pharmaceutical Intermediate Preparation
N-α -1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)ethyl-D-2,3-diaminopropionic acid is appropriate for pharmaceutical intermediate preparation where chiral amino acid derivatives and rigidified scaffolds are used to build peptidomimetic or heterocycle-containing intermediates. The presence of a free carboxylic acid enables formation of coupling-ready activated derivatives for downstream synthetic routes, while the diamino functionality supports staged conversion into protected intermediates that can survive multi-step manufacturing sequences. The cyclohexanedione-rich ylidene substituent can be leveraged as a scaffold element that modulates physicochemical properties and can participate in further transformations to generate drug-like fragments. Stereochemical fidelity at the D-center supports consistent structure definition across process batches, and orthogonal protection strategies for the two amines support chemoselective functionalization during intermediate elaboration. This makes the compound a useful chiral building block for fine chemical synthesis and process chemistry intermediate development aligned with peptide- and peptidomimetic-oriented manufacturing.
5. Analytical Research Standards
N-α -1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)ethyl-D-2,3-diaminopropionic acid can be employed in analytical research as a structurally defined amino acid derivative standard for method development and impurity profiling. The combination of a D-configured diamino acid core and the distinctive cyclohexanedione ylidene substituent yields a characteristic chromatographic and spectroscopic signature that can support identification of related protected amino acid intermediates and coupling byproducts. The carboxylic acid and nitrogen functionalities allow derivatization into detectable forms for LC-MS or chromatographic workflows, while the carbonyl-rich motif can enhance detectability under conditions sensitive to carbonyl-containing scaffolds. Protection-state control enables preparation of reference materials corresponding to specific synthetic stages, including N-protected or side-chain-protected forms. This analytical utility supports quality-focused development of amino acid derivatization and peptide coupling processes, including monitoring of stereochemically relevant intermediates.
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