N-α-Boc-N-β-1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)ethyl-D-2,3-diaminopropionic acid is a protected, amino acid-derived building block featuring a D-2,3-diaminopropionic acid backbone bearing an N-α Boc protecting group and an N-β substituent that includes a 4,4-dimethyl-2,6-dioxocyclohex-1-ylidene (cyclohexanedione-derived) moiety. The molecule contains amino functionality on the 2,3-diaminopropionic acid framework and a carboxylic acid group, while the Boc group masks the α-amino reactivity and the cyclic dioxo substituent provides a conjugated, carbonyl-rich structural element that can influence chemoselectivity and downstream derivatization. In peptide and amino acid synthesis workflows, this protected analogue is used as a controlled-reactivity precursor for assembling modified peptide backbones or for preparing structurally defined amino acid derivatives for structure-activity studies and analytical method development.
CAT No: CP05816
N-α-Boc-N-β-1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)ethyl-D-2,3-diaminopropionic acid is a D-configured amino acid derivative featuring a protected α-amino group (Boc) and a β-amino substituent embedded in a substituted cyclohexane-1-ylidene scaffold bearing two ketone functionalities (2,6-dioxo) and a gem-dimethyl motif at C-4. The structure contains an α-carboxylic acid for peptide coupling chemistry and two closely positioned amino functionalities (α-protected and β-amino) that can be differentially addressed through orthogonal protection and selective deprotection strategies. The rigid, electrophile-bearing cyclic enedione/ylidene motif can participate in downstream derivatization and scaffold elaboration while maintaining stereochemical integrity at the amino acid center(s). As a chiral amino acid intermediate and peptide building block, it supports protected amino acid synthesis workflows where Boc removal and subsequent acylation enable controlled incorporation into peptide analogs and other nitrogen-rich molecular frameworks.
1. Protected Peptide Building Blocks
N-α-Boc-N-β-1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)ethyl-D-2,3-diaminopropionic acid supports protected peptide synthesis by combining an α-carboxylic acid with a Boc-protected α-amino group that can be removed under acidic conditions to reveal a coupling-ready amine. The D-configuration and the β-amino substituent allow incorporation into peptide coupling sequences where side-chain functionality and stereochemical fidelity are required for structure-activity relationship studies and peptidomimetic construction. The cyclic 2,6-dioxo cyclohexylidene motif can be retained through amide bond formation, enabling generation of peptide analogs that carry a rigid, carbonyl-rich pharmacophore-like element. Downstream, the resulting protected-to-deprotected transitions facilitate stepwise assembly of multi-amino-acid sequences and preparation of defined peptide fragments for biochemical research.
2. Unnatural Amino Acid Incorporation
N-α-Boc-N-β-1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)ethyl-D-2,3-diaminopropionic acid functions as an unnatural amino acid incorporation reagent for chemical biology and peptide engineering programs that require non-proteinogenic stereochemistry and engineered side-chain topology. The D-2,3-diaminopropionic acid framework provides a controlled arrangement of amino groups, while the Boc strategy enables selective activation of the α-nitrogen for peptide bond formation without prematurely engaging the β-amino site. The β-amino linkage to the substituted cyclohexane-ylidene enedione scaffold introduces a carbonyl-rich, conformationally constrained element that can influence local conformation and molecular recognition in peptide analogs. The compound can be applied to construct stereochemically defined libraries for SAR studies, where subsequent functional group transformations on the cyclic ketones may support analog diversification.
3. Bioconjugation Linker Chemistry
N-α-Boc-N-β-1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)ethyl-D-2,3-diaminopropionic acid can be used in bioconjugation chemistry where amino acid-derived handles enable attachment to biomolecular scaffolds while preserving stereochemical definition. The presence of a protected α-amine and a free carboxylic acid supports conversion into activated derivatives for amide or carbamate formation, enabling coupling to lysine-containing proteins, peptide carriers, or polymer backbones after Boc deprotection and appropriate activation. The cyclic 2,6-dioxo motif may serve as a platform for further derivatization, including generation of electrophilic or carbonyl-reactive functionalities that can be tuned for conjugation workflows. Downstream conjugates prepared from this amino acid derivative can be used as defined labeling reagents, molecular probes, or scaffold fragments in biochemical research and protein engineering studies.
4. Process Chemistry Intermediate
N-α-Boc-N-β-1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)ethyl-D-2,3-diaminopropionic acid is suitable for process chemistry intermediate preparation due to its clear orthogonality pattern between a Boc-protected amine and an acid group that can be selectively transformed during manufacturing route design. The rigid cyclohexane-ylidene diketone substituent provides a stable carbonyl framework that can withstand peptide-coupling conditions when protected appropriately, supporting stepwise synthesis of nitrogen-rich intermediates used in fine chemical production. Boc protection supports controlled deprotection and subsequent coupling operations, allowing manufacturing sequences that separate amine-unmasking from acylation steps to manage reactivity. The compound's chiral amino acid character makes it applicable to scalable synthesis of peptide building blocks and peptidomimetic fragments where stereochemical consistency is required across batches.
5. Analytical Standards And SAR Probes
N-α-Boc-N-β-1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)ethyl-D-2,3-diaminopropionic acid can serve as an analytical research reference and SAR probe intermediate because its D-stereochemistry and protected functional groups generate well-defined chromatographic and mass spectrometric signatures. The combination of Boc-protected α-amino functionality, carboxylic acid, and the carbonyl-rich cyclohexane-ylidene motif supports targeted detection of peptide fragments and amino acid derivatives during method development for peptide synthesis monitoring. The compound can be applied to prepare defined standards for purity checks, identity verification, and fragment-based characterization of peptide analogs that incorporate this chiral building block. Broader relevance extends to synthetic methodology development in amino acid chemistry, where structurally constrained, stereodefined intermediates help correlate coupling outcomes with downstream peptidomimetic structure.
1. An Open-label, Single-center, Safety and Efficacy Study of Eyelash Polygrowth Factor Serum
4. SERS spectrum of the peptide thymosin‐β4 obtained with Ag nanorod substrate
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