N-α-Fmoc-N-γ-1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)-3-methylbutyl-D-2,4-diaminobutyric acid is a protected, non-proteinogenic amino acid derivative featuring an Fmoc carbamate on the α-amino group and a D-2,4-diaminobutyric acid core bearing additional amino functionality at the 2- and 4-positions. The molecule contains a side-chain substituted with a 1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene) group and a 3-methylbutyl substituent, providing a constrained, carbonyl-rich cyclic enone-like motif while retaining a free carboxyl group and stereochemical specification at the D center indicated in the name. In peptide chemistry and chemical biology workflows, this protected analogue functions as a stepwise building block for introducing the substituted diaminobutyric residue into peptide or peptidomimetic structures, supporting controlled chemoselectivity of the α-amino functionality during coupling and enabling downstream derivatization or analytical differentiation based on the distinctive side-chain handle.
CAT No: CP05329
N-α-Fmoc-N-γ-1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)-3-methylbutyl-D-2,4-diaminobutyric acid is a D-configured, diamino acid derivative designed for protected peptide-building-block chemistry, bearing an N-α Fmoc group for base-labile solid-phase compatible activation. The side-chain architecture includes an additional amino functionality (2,4-diaminobutyric acid motif) and a γ-substituent that is masked as a cyclic urea/ketone-derived ylidene unit, while the molecule also contains a stereogenic center that governs incorporation outcomes during peptide coupling. The presence of multiple carbonyl groups within the γ-ylidene moiety and the protected amine pattern modulate nucleophilicity and chemoselectivity, enabling controlled deprotection and subsequent functional group unveiling. The overall reactivity profile supports stepwise N-protection strategies, orthogonal deprotection planning, and downstream conversion into peptide analogs and synthetic intermediates for structure-driven studies.
1. Fmoc Peptide Synthesis
N-α-Fmoc-N-γ-1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)-3-methylbutyl-D-2,4-diaminobutyric acid is applied in Fmoc-based peptide synthesis where the N-α Fmoc group enables base-mediated removal and subsequent amide bond formation. The D-2,4-diaminobutyric acid backbone provides an amino acid core that can be incorporated as a chiral residue, while the additional side-chain amino functionality is preorganized for controlled coupling or later derivatization after orthogonal deprotection. The γ-ylidene protecting/attenuating substituent, together with the embedded carbonyl-rich ring system, supports chemoselective handling by reducing undesired side reactions during activation and coupling steps. The resulting peptide building block can be used to generate peptide sequences and peptidomimetic scaffolds that require defined stereochemistry and protected diamino functionality for iterative chain elongation.
2. Amino Acid Side-Chain Functionalization
N-α-Fmoc-N-γ-1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)-3-methylbutyl-D-2,4-diaminobutyric acid supports amino acid derivatization workflows targeting side-chain functionalization of diamino acid motifs. The molecule's two nitrogen sites, combined with the γ-ylidene masked group, can be used to plan orthogonal unmasking events that reveal one or both amines in a controlled sequence. The carbonyl-containing γ moiety can act as a handle for downstream transformations or for tuning solubility and reactivity during intermediate isolation and purification. The protected amino acid derivative thus serves as a chiral intermediate for constructing modified amino acid residues, generating peptide analogs with tailored charge distribution, and enabling subsequent conjugation-ready amine presentation.
3. Chemical Biology And Labeling
N-α-Fmoc-N-γ-1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)-3-methylbutyl-D-2,4-diaminobutyric acid is suitable for chemical biology research that requires defined stereochemical incorporation of diamino acid elements into protein-interaction probes. The protected amine pattern and Fmoc-bearing N-terminus allow stepwise synthesis of labeled peptides or peptide-like ligands where functional groups can be introduced after sequence assembly. The D-configuration contributes to predictable conformational and recognition behavior in peptide scaffolds, while the γ-ylidene carbonyl-rich substituent can help maintain stability during synthesis and storage before final deprotection. The compound can be employed as a chiral building block to prepare conjugation-ready peptide fragments for subsequent bioconjugation strategies and molecular recognition studies in biochemical assays.
4. Peptidomimetics And SAR Studies
N-α-Fmoc-N-γ-1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)-3-methylbutyl-D-2,4-diaminobutyric acid is used in peptidomimetic construction and structure-activity relationship studies where diamino acid residues are incorporated to modulate binding and selectivity. The stereogenic D-center and the presence of multiple nitrogens enable systematic variation of side-chain protonation states and hydrogen-bonding patterns across analog series. The γ-ylidene substituent, together with the amine protection scheme, supports controlled synthesis of analogs that preserve chemoselectivity during coupling while allowing later unmasking to generate specific functional group presentations. The resulting peptide analogs can be used as chemically defined SAR probes to interrogate how protected diamino acid geometry and functional group density influence molecular recognition.
5. Process Chemistry Intermediate
N-α-Fmoc-N-γ-1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)-3-methylbutyl-D-2,4-diaminobutyric acid is relevant to process chemistry and fine chemical synthesis as a protected, stereodefined amino acid intermediate for manufacturing peptide building blocks. The Fmoc group provides a robust protection strategy compatible with scalable peptide coupling workflows, while the γ-ylidene masking group and carbonyl-rich ring system help control reactive amine behavior during intermediate handling and purification. The diamino acid framework supports downstream conversion into multiple derivatives through selective deprotection and subsequent functional group installation, aligning with route design for producing diverse peptide analogs. The compound's protected structure therefore can be employed as a chiral feedstock for industrial peptide intermediate preparation and for supplying consistent stereochemical inputs to downstream synthetic manufacturing of amino acid-derived products.
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