N-α-Fmoc-N-γ-1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)ethyl-D-2,4-diaminobutyric acid is a protected, non-proteinogenic amino acid derivative featuring a D-configured 2,4-diaminobutyric acid backbone bearing an N-α Fmoc protecting group and an N-γ substituted 1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)ethyl moiety. The molecule contains an amino acid framework with a carboxyl functional group and two amino functionalities at the 2- and 4-positions, while the additional N-γ substitution and the Fmoc group modulate chemoselectivity by masking nucleophilicity during stepwise assembly. In peptide and peptidomimetic synthesis workflows, it functions as a protected building block for introducing a diamino butyric residue with a constrained, carbonyl-rich cyclic "ylidene" substituent that provides a defined side-chain environment for structure-activity studies and analytical characterization of modified peptide architectures.
CAT No: CP05325
N-α-Fmoc-N-γ-1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)ethyl-D-2,4-diaminobutyric acid is an Fmoc-protected, stereodefined amino acid derivative bearing a D-2,4-diaminobutyric acid backbone and an additional N-substituted γ-amino functionality. The molecule contains an N-terminal Fmoc carbamate that supports solid-phase peptide synthesis compatibility, alongside a γ-amino group masked as a 1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)ethyl (Dioxocyclohexylidene) imine-type protecting motif that can modulate nucleophilicity during peptide assembly. The 2,6-dioxocyclohexylidene substituent introduces two carbonyl groups and a rigid cyclic framework, which can influence conformational behavior and chemoselectivity under coupling and deprotection conditions. The presence of multiple amine sites and a chiral center makes the compound a targeted chiral amino acid intermediate for controlled side-chain functionalization and downstream derivatization into polyamine-rich peptide analogs and constrained peptidomimetics.
1. Protected Amino Acid Synthesis
N-α-Fmoc-N-γ-1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)ethyl-D-2,4-diaminobutyric acid is applied in protected amino acid chemistry and chiral intermediate preparation where orthogonal protection is required for diamino acid handling. The N-terminal Fmoc group enables standard peptide coupling workflows while the γ-amino protection by the dioxocyclohexylidene motif provides a controlled strategy to suppress side-chain reactivity during early synthetic steps. The carbonyl-rich cyclic protecting group can be selected to tune chemoselectivity, supporting stepwise exposure of amine functionality for subsequent derivatization. Downstream use includes conversion into sequence-defined building blocks for diamino acid incorporation and manufacturing-relevant intermediate preparation for fine chemical synthesis.
2. Peptide Synthesis
N-α-Fmoc-N-γ-1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)ethyl-D-2,4-diaminobutyric acid is suitable for peptide building block preparation and solid-phase peptide synthesis programs that require a D-configured diamino acid residue. The Fmoc carbamate supports Nα activation and coupling while the protected γ-amino site can remain masked to prevent branching or undesired crosslinking during chain elongation. The D-2,4-diaminobutyric acid architecture introduces a second nitrogen handle that, after selective deprotection, can be used for intramolecular cyclization, side-chain conjugation, or incorporation into polyamine-like motifs. Resulting peptide products can serve as controlled scaffolds for peptide chemistry, peptidomimetic construction, and structure-guided optimization of backbone and side-chain presentation.
3. Chemical Biology Conjugation
N-α-Fmoc-N-γ-1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)ethyl-D-2,4-diaminobutyric acid supports chemical biology workflows that require orthogonally addressable amine functionality for biomolecule modification. The molecule's protected γ-amino group can be leveraged to manage chemoselective conjugation timing, while the D-configured diamino backbone can introduce defined cationic character after exposure of the side-chain amine. The carbonyl-containing cyclic protecting motif provides a handle for controlled unmasking strategies that can reduce side reactions during conjugation to proteins, nucleic acids, or targeting ligands. Downstream applications include generation of labeled peptides, affinity probes, and chemically defined bioconjugates where stereochemistry and amine spacing influence molecular recognition and labeling reproducibility.
4. Peptidomimetics And SAR Studies
N-α-Fmoc-N-γ-1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)ethyl-D-2,4-diaminobutyric acid is used in peptidomimetic design and SAR studies to incorporate a stereochemically defined diamino acid unit into constrained or functionalized scaffolds. The rigid, carbonyl-rich dioxocyclohexylidene substituent and the D-configuration can be applied to tune conformational preferences and side-chain orientation, which is relevant for mapping how amine placement affects binding and activity profiles in structure-activity relationship investigations. The ability to selectively unmask the γ-amino group enables formation of additional amide, urea, or cyclic derivatives that expand chemical space beyond standard amino acid residues. Resulting analogs can be employed for fragment-to-lead optimization, molecular design campaigns, and systematic evaluation of backbone stereochemistry and side-chain reactivity patterns.
5. Pharmaceutical Intermediate Preparation
N-α-Fmoc-N-γ-1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)ethyl-D-2,4-diaminobutyric acid can function as a process chemistry intermediate for manufacturing routes that require protected diamino acid building blocks with controlled deprotection sequencing. The Fmoc-protected N-terminus supports reproducible peptide-coupling compatibility, while the γ-amino masking group provides a strategy to manage multiple amine reactivity during scale-up and purification. The presence of carbonyl groups and a defined cyclic protecting framework can aid in designing robust synthetic steps that minimize undesired oligomerization or overreaction of free amines. Downstream utility includes supplying protected amino acid derivatives for fine chemical production, peptide-based intermediate generation, and controlled synthesis of polyamine-containing drug candidates or research-grade analogs.
6. Analytical Standards And Method Development
N-α-Fmoc-N-γ-1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)ethyl-D-2,4-diaminobutyric acid is applicable to analytical research and method development where defined stereochemistry and protected functional groups are required for characterization. The Fmoc chromophore and the carbonyl-rich protecting motif provide distinct analytical signatures that can support LC-MS, HPLC, and derivatization-based workflows for monitoring protected amino acid intermediates and peptide coupling outcomes. The D-2,4-diaminobutyric acid scaffold enables preparation of reference materials that reflect side-chain amine behavior after controlled deprotection, supporting verification of identity and chemoselective unmasking performance. Broader relevance includes use as a defined chiral building block for impurity profiling, process monitoring, and development of reliable analytical methods for amino acid derivative manufacturing.
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