N-α-Fmoc-N-γ-1-(4,4-dimethyl-2,6-dioxocyclohex-1 -ylidene)-3-methylbutyl-L-2,4-diaminobutyric acid is a protected, amino acid derivative featuring an Fmoc carbamate on the α-amino group and an L-2,4-diaminobutyric acid core bearing an additional 2,4-diamino motif. The molecule contains a free carboxyl group and a side-chain guanidinium-like diamino functionality whose reactivity is modulated by the N-γ substitution with a 4,4-dimethyl-2,6-dioxocyclohex-1-ylidene moiety, while the 3-methylbutyl substituent further defines the steric and hydrophobic character of the protected nitrogen. In peptide chemistry and chemical biology workflows, this compound functions as a stepwise building block where the Fmoc group supports controlled amide bond formation and the N-γ modification provides chemoselectivity for incorporating a substituted diaminobutyric acid residue into larger peptide or peptidomimetic structures.
CAT No: CP05330
N-α-Fmoc-N-γ-1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)-3-methylbutyl-L-2,4-diaminobutyric acid is an Fmoc-protected, chiral amino acid derivative built on an L-2,4-diaminobutyric acid backbone. The molecule contains an N-terminal fluorenylmethoxycarbonyl (Fmoc) protecting group for controlled peptide coupling, while the side-chain bears a γ-amino substituent masked as a 1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene) imide/urea-type functionality and a 3-methylbutyl substituent that modulates sterics and reactivity. Two amino functionalities are present in the underlying scaffold, with one protected for orthogonal chemistry and the other engaged in a carbonyl-rich masking group that can be unmasked under peptide-chemistry deprotection conditions. The carbonyl density and the cyclic imide-like motif provide distinct polarity and hydrogen-bonding characteristics, making the compound a structured, stereodefined intermediate for assembling protected amino acid building blocks, peptide analogs, and downstream functionalized derivatives.
1. Protected Amino Acid Synthesis
N-α-Fmoc-N-γ-1-(4,4-dimethyl-2,6-dioxocyclohex-1 -ylidene)-3-methylbutyl-L-2,4-diaminobutyric acid is used in protected amino acid synthesis workflows where orthogonal protection and side-chain masking are required for controlled coupling. The Fmoc group on the α-nitrogen supports standard base-mediated deprotection to generate a reactive amino terminus for peptide coupling, while the γ-amino is incorporated into a carbonyl-rich cyclic masking motif that can remain stable during common coupling steps and be removed in later stages. The L stereocenter on the 2,4-diaminobutyric acid framework enables stereochemically defined incorporation into peptide sequences and peptidomimetic scaffolds. The resulting protected amino acid intermediate can be carried through multistep synthesis as a chiral building block for fine chemical production and research-grade peptide construction.
2. Peptide Synthesis
N-α-Fmoc-N-γ-1-(4,4-dimethyl-2,6-dioxocyclohex-1 -ylidene)-3-methylbutyl-L-2,4-diaminobutyric acid is applied as a peptide building block in solid-phase or solution-phase peptide synthesis where a diamino acid motif and controlled side-chain functionality are needed. The Fmoc-protected α-amine enables sequential N-terminal deprotection and coupling, while the side-chain masking group helps manage chemoselectivity by limiting premature reactions of the additional amino functionality. The carbonyl-rich 4,4-dimethyl-2,6-dioxocyclohex-1-ylidene unit can influence local conformation and solubility of the growing peptide, which may affect coupling behavior and purification profiles. The 3-methylbutyl substituent provides hydrophobic character that can be leveraged to tune peptide folding propensity and to generate structured analogs for downstream biochemical studies.
3. Chemical Biology Labeling
N-α-Fmoc-N-γ-1-(4,4-dimethyl-2,6-dioxocyclohex-1 -ylidene)-3-methylbutyl-L-2,4-diaminobutyric acid is suitable for chemical biology research requiring incorporation of protected diamino acid residues into probes, linkers, or constrained peptide frameworks. The presence of an Fmoc-protected α-amine supports stepwise assembly of labeled peptides, while the masked γ-amino functionality can be unmasked at a chosen stage to enable selective conjugation to electrophiles, activated esters, or carbonyl-reactive tags. The cyclic dioxocyclohexylidene motif introduces a defined polarity pattern that can assist in controlling nonspecific interactions during probe synthesis and subsequent purification. The chiral, side-chain-functionalized residue can therefore serve as a platform for generating derivatized peptide tools used in molecular recognition studies and biochemical assay development.
4. Peptidomimetics And SAR Studies
N-α-Fmoc-N-γ-1-(4,4-dimethyl-2,6-dioxocyclohex-1 -ylidene)-3-methylbutyl-L-2,4-diaminobutyric acid is employed in peptidomimetic construction for structure-activity relationship studies where diamino acid geometry and side-chain masking are leveraged to control analog properties. The L-2,4-diaminobutyric acid backbone provides a stereodefined scaffold that can be incorporated into constrained or modified peptide-like molecules, while the protected γ-amino functionality allows systematic variation of side-chain reactivity across an analog series. The 3-methylbutyl substituent contributes hydrophobic bulk that can be used to probe binding pocket complementarity and to tune conformational preferences in SAR workflows. Downstream deprotection and functional group transformation of the masked amino site can enable generation of a library of analogs with distinct charge and hydrogen-bonding patterns, supporting iterative medicinal chemistry and biochemical characterization.
5. Pharmaceutical Intermediate Preparation
N-α-Fmoc-N-γ-1-(4,4-dimethyl-2,6-dioxocyclohex-1 -ylidene)-3-methylbutyl-L-2,4-diaminobutyric acid is relevant to pharmaceutical intermediate preparation where protected, stereodefined amino acid derivatives are manufactured for incorporation into peptide-based or peptide-like active ingredients. The Fmoc group provides a robust handle for controlled N-terminal activation during synthesis of higher-order intermediates, while the carbonyl-rich side-chain masking group supports chemoselective processing by reducing undesired side reactions of additional amino functionality. The defined chiral center and the stable protecting-group architecture can be aligned with process chemistry needs for reproducible intermediate formation and predictable downstream deprotection. The compound can thus function as a manufacturing-grade chiral building block for fine chemical synthesis of protected sequences and for producing intermediates that later undergo functionalization steps to reach final targeted structures.
6. Process Chemistry And Peptide Manufacturing
N-α-Fmoc-N-γ-1-(4,4-dimethyl-2,6-dioxocyclohex-1 -ylidene)-3-methylbutyl-L-2,4-diaminobutyric acid is applicable to process chemistry and peptide manufacturing development where orthogonally protected amino acid inputs are required for scalable assembly. The Fmoc-protected α-amine supports standardized deprotection/coupling cycles, and the side-chain masking group provides a controlled reactivity profile that can reduce side-product formation during multistep peptide chain growth. The presence of multiple carbonyl groups and a cyclic masking motif can influence solubility and handling characteristics, which are practical considerations in manufacturing-scale synthesis and purification planning. The resulting protected amino acid building block can be incorporated into defined synthetic routes to produce peptide intermediates and functionalized derivatives used in industrial fine chemical production and applied peptide science.
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