N-α-Boc-N-γ-1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)ethyl-D-2,4-diaminobutyric acid is a Boc-protected, D-stereochemically defined amino acid derivative in which the 2,4-diaminobutyric acid backbone bears an N-α tert-butoxycarbonyl protecting group and a substituted N-γ side-chain functionality. The molecule contains a carboxylic acid group and multiple amino substituents, with the N-γ position linked to a 4,4-dimethyl-2,6-dioxocyclohex-1-ylidene (cyclohexanedione-derived) moiety that introduces a conjugated, carbonyl-rich structural element while maintaining the amino acid framework. In synthesis and chemical biology workflows, this protected diamino acid analogue is used as a defined precursor for stepwise peptide or peptidomimetic assembly and for preparing structured amino acid derivatives where controlled chemoselectivity and a side-chain functional handle are required.
CAT No: CP05311
N-α-Boc-N-γ-1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)ethyl-D-2,4-diaminobutyric acid is a D-configured, diamino acid derivative in which the α-amino group is protected as a Boc carbamate and the γ-amino functionality is substituted with a 1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)ethylidene-bearing motif. The molecule contains a free carboxylic acid for peptide coupling chemistry and a second amino handle that can be selectively functionalized depending on orthogonal protection and activation conditions. The appended cyclohexenone-like dioxo substituent introduces a rigid, electrophilically activated carbonyl environment that can participate in derivatization and downstream scaffold elaboration, while the stereogenic centers associated with the D-2,4-diaminobutyric acid core support stereochemically defined peptide analog construction. Boc protection provides controlled N-deprotection compatibility, enabling sequential assembly strategies in peptide synthesis and enabling access to amino acid building blocks and chiral intermediates for fine chemical and biochemical research workflows.
1. Protected Amino Acid Chemistry
N-α-Boc-N-γ-1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)ethyl-D-2,4-diaminobutyric acid serves as a protected amino acid derivative for orthogonal N-functionalization and stepwise synthesis of chiral intermediates. The Boc-protected α-amine and the free carboxylic acid support standard peptide coupling logic, while the additional amino functionality can be directed toward selective acylation, carbamate formation, or salt formation to tune reactivity. The appended 4,4-dimethyl-2,6-dioxocyclohex-1-ylidene substituent can undergo further chemical transformation as a carbonyl-rich motif, enabling conversion into diversified analogs after incorporation. Stereochemical definition of the D-2,4-diaminobutyric acid framework helps maintain stereochemical integrity through protected amino acid synthesis and downstream derivatization.
2. Peptide Synthesis
N-α-Boc-N-γ-1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)ethyl-D-2,4-diaminobutyric acid functions as a peptide building block for incorporation of a D-configured diamino acid unit into protected peptide chains. The Boc carbamate at the α-nitrogen supports controlled deprotection timing during iterative coupling, while the carboxylic acid enables amide bond formation with appropriately activated partners. The γ-substituted, cyclohexane-dione-derived side-chain motif can be retained as a structural element for peptidomimetic design or used as a handle for post-coupling modification, depending on the chosen orthogonal protection scheme for the second amino group. Defined stereochemistry at the amino acid core supports construction of peptide analogs with consistent three-dimensional presentation for structure-activity relationship studies and biochemical probe development.
3. Peptidomimetics And SAR Studies
N-α-Boc-N-γ-1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)ethyl-D-2,4-diaminobutyric acid can be applied in peptidomimetic construction where rigid, carbonyl-rich side-chain features influence conformational behavior. The diamino acid backbone provides a platform for generating constrained analogs, while the Boc-protected α-amine and the γ-substituted amino linkage enable systematic variation of N-substitution patterns during library synthesis. The cyclohex-1-ylidene dioxo motif may participate in subsequent functional group transformations, allowing access to electrophile-bearing or carbonyl-activated derivatives used to probe binding interactions. Stereodefined incorporation of the D-configuration supports consistent comparative SAR studies across analog series built from amino acid derivatization and peptide coupling chemistry.
4. Chemical Biology Probes
N-α-Boc-N-γ-1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)ethyl-D-2,4-diaminobutyric acid is suitable for chemical biology research intermediate preparation where amino acid-derived conjugation handles are required. The protected α-amine and carboxylic acid allow controlled conversion into activated derivatives for conjugation workflows, while the second amino functionality can be tuned for orthogonal labeling strategies using protection-group manipulation. The carbonyl-rich cyclohexenone-like substituent can serve as a structural reporter element or as a platform for further derivatization into functional groups compatible with probe scaffolds. D-configuration and the defined side-chain architecture help maintain stereochemical fidelity in biomolecule-modifying constructs, supporting reproducible probe synthesis from amino acid chemistry.
5. Process Chemistry Intermediate
N-α-Boc-N-γ-1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)ethyl-D-2,4-diaminobutyric acid can be employed as a chiral amino acid intermediate in process chemistry for manufacturing route design toward protected amino acid derivatives and peptide-related fine chemicals. The Boc carbamate provides a robust, acid-labile protection strategy that can be managed during multi-step sequences, while the carboxylic acid supports predictable activation chemistry for downstream coupling or salt formation. The presence of a second amino group enables selective derivatization steps that can be aligned with orthogonal protection and purification requirements in industrial synthesis planning. The stereochemically defined D-2,4-diaminobutyric acid core supports reproducible chiral building block preparation for specialty chemical production and peptide analog manufacturing.
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