N-α-Fmoc-N-β-1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)-3-methylbutyl-L-2,3-diaminopropionic acid is a protected, amino-acid-derived building block in which the α-amino group is capped with an Fmoc group and the side-chain nitrogen is part of a 2,3-diaminopropionic acid framework. The molecule contains a free carboxyl functional group alongside two amino functionalities, and it bears a substituted cyclohexane-2,6-dione (dioxocyclohex-1-ylidene) moiety that is linked via a ylidene-type carbon framework to the β-substituent, with the name indicating an L configuration at the 2,3-diaminopropionic acid center. In peptide and peptidomimetic synthesis, this protected amino acid derivative functions as a stepwise coupling precursor where the Fmoc group controls chemoselectivity at the α-amino position while the additional side-chain substitution provides a defined handle for constructing complex, nitrogen-rich residues for structure-activity studies and chemical biology labeling strategies.
CAT No: CP05840
N-α-Fmoc-N-β-1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)-3-methylbutyl-L-2,3-diaminopropionic acid is an Fmoc-protected, chiral amino acid derivative of L-2,3-diaminopropionic acid in which the β-amino functionality is substituted with a bulky, cyclic urea-like "ylidene" group and a 3-methylbutyl side chain. The structure contains an N-terminal Fmoc carbamate for base-labile protection, a stereogenic amino acid backbone, and two adjacent amino groups that can be selectively managed through orthogonal protection and controlled deprotection. The 2,6-dioxocyclohex-1-ylidene motif introduces strongly electron-withdrawing carbonyl functionality that can influence coupling reactivity and downstream transformations, while the hydrophobic 3-methylbutyl substituent supports incorporation into peptide-like scaffolds and hydrophobic SAR motifs. The compound is engineered as a peptide synthesis-compatible chiral building block that can participate in amide bond formation after appropriate activation and protecting-group strategy design.
1. Protected Amino Acid Synthesis
N-α-Fmoc-N-β-1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)-3-methylbutyl-L-2,3-diaminopropionic acid is used in protected amino acid chemistry to establish an orthogonally addressable N-terminus and a controlled β-amino environment. The Fmoc carbamate enables routine solid-phase or solution-phase peptide coupling workflows via base-mediated removal, while the substituted β-amino substituent and the adjacent diamino architecture support selective derivatization planning. The presence of multiple carbonyl groups within the cyclic ylidene fragment can be leveraged to tune solubility and influence subsequent synthetic steps that require stable intermediates. The resulting protected amino acid derivative can serve as a defined chiral intermediate for preparing peptide building blocks and for constructing downstream functionalized amino acid analogs.
2. Peptide Synthesis
N-α-Fmoc-N-β-1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)-3-methylbutyl-L-2,3-diaminopropionic acid is applied as a peptide building block in peptide synthesis where the Fmoc-protected N-terminus supports stepwise chain assembly. The L-2,3-diaminopropionic acid backbone provides a stereochemically defined residue that can be incorporated into peptide-like sequences, while the substituted β-amino functionality can be managed to control chemoselectivity during coupling and subsequent transformations. The bulky cyclic ylidene carbonyl system and the hydrophobic 3-methylbutyl substituent can help stabilize conformations and introduce side-chain character that is relevant for peptidomimetic design. The compound's protected amino acid form is suitable for generating defined peptide analogs and for producing protected intermediates used in iterative synthesis toward complex, functionalized oligomers.
3. Chemical Biology Probes
N-α-Fmoc-N-β-1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)-3-methylbutyl-L-2,3-diaminopropionic acid is suitable for chemical biology research programs that require amino acid-derived probes with controlled functional-group presentation. The diamino backbone enables conjugation-site engineering through selective protection/deprotection logic, and the Fmoc group provides a handle for controlled exposure of the N-terminus during scaffold assembly. The cyclic dicarbonyl ylidene motif can serve as a chemically distinctive feature for incorporation into labeled peptide analogs used in binding studies, affinity reagent construction, or probe libraries. The resulting labeled or functionalized derivatives can be assembled into peptide mimics that maintain stereochemical fidelity while enabling downstream attachment of tags or reactive groups for biomolecular interaction studies.
4. Peptidomimetics And SAR Studies
N-α-Fmoc-N-β-1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)-3-methylbutyl-L-2,3-diaminopropionic acid is used in peptidomimetic construction and structure-activity relationship studies where side-chain bulk, carbonyl-rich functionality, and stereochemistry influence molecular recognition. The 3-methylbutyl substituent contributes hydrophobic character, while the 4,4-dimethyl-2,6-dioxocyclohex-1-ylidene fragment introduces a rigid, electron-withdrawing element that can modulate hydrogen-bonding patterns and conformational preferences. The Fmoc-protected N-terminus supports systematic analog generation by enabling consistent coupling chemistry across a series of residues. The compound can therefore be incorporated into SAR-focused peptide analogs and fragment-like scaffolds to generate defined stereochemical variants for comparative evaluation of structure-function relationships in applied medicinal chemistry workflows.
5. Process Chemistry Intermediate
N-α-Fmoc-N-β-1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)-3-methylbutyl-L-2,3-diaminopropionic acid is employed as a chiral process chemistry intermediate for specialty chemical production routes that require protected amino acid inputs with robust handling characteristics. The Fmoc carbamate provides a stable, isolable protection strategy that can be removed under controlled conditions to reveal the reactive amine for subsequent coupling or derivatization steps. The presence of multiple carbonyl groups and a substituted β-amino environment supports designing manufacturing sequences that minimize undesired side reactions by using orthogonal protection logic and chemoselective activation. The compound's defined stereochemistry and peptide-compatible protected form make it suitable for scaling synthetic sequences that generate amino acid derivatives for downstream peptide manufacturing, peptidomimetic intermediate preparation, and fine chemical synthesis programs.
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