N-α-Fmoc-N-δ-1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)-3-methylbutyl-D-ornithine is a protected, non-natural ornithine derivative designed for peptide chemistry, featuring the ornithine α-amino acid backbone with an Fmoc group on the α-nitrogen and a substituted δ-side-chain nitrogen. The δ-amino functionality is incorporated into a cyclic ketone-derived ylidene substituent (4,4-dimethyl-2,6-dioxocyclohex-1-ylidene) and further substituted with a 3-methylbutyl group, while the molecule contains both an α-carboxyl group and the protected amine framework; the D stereochemical configuration is explicitly indicated for the amino acid center. In synthesis, the Fmoc-protected α-amino group supports stepwise assembly of peptide sequences on solid phase or in controlled solution-phase coupling workflows, while the bulky, carbonyl-rich δ-substitution provides a defined side-chain architecture for structure-activity studies, chemical biology probe construction, or the preparation of ornithine-based peptide analogues.
CAT No: CP08719
N-α-Fmoc-N-δ-1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)-3-methylbutyl-D-ornithine is an Fmoc-protected, D-configured ornithine derivative designed for orthogonally addressable peptide chemistry. The molecule contains an Fmoc carbamate on the α-amino group for controlled N-terminal protection, while the δ-amino site is substituted with a bulky 1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene) group that can function as a protected, conjugation-ready handle and a steric element for selective coupling behavior. The side chain bears a 3-methylbutyl substituent, introducing a hydrophobic stereochemical environment that can influence conformational preferences in peptide analogs and peptidomimetics. The presence of two ring carbonyls within the cyclohexenylidene motif provides strong electrophile/amide-adjacent reactivity patterns for downstream derivatization, while the overall protected amino acid architecture supports compatibility with standard protected amino acid synthesis and peptide building block preparation workflows.
1. Peptide Synthesis
N-α-Fmoc-N-δ-1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)-3-methylbutyl-D-ornithine serves as a protected amino acid building block for solid-phase peptide synthesis and related coupling strategies. The Fmoc carbamate enables N-terminal deprotection under base conditions to expose a reactive α-amino group for stepwise peptide bond formation, while the δ-substitution maintains controlled chemoselectivity at the side-chain nitrogen during chain assembly. The D-ornithine stereocenter and the 3-methylbutyl side chain can be incorporated to tune backbone stereochemistry and side-chain hydrophobicity in peptide scaffolds. The cyclohexenylidene carbonyl motif can be retained through assembly and then transformed post-coupling, supporting construction of peptide analogs and constrained side-chain variants used in amino acid derivatization studies.
2. Side-Chain Functionalization
N-α-Fmoc-N-δ-1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)-3-methylbutyl-D-ornithine is suited for side-chain functionalization workflows where the δ-amino functionality is masked yet structurally informative. The δ-substitution with a carbonyl-rich cyclohexenylidene group provides a defined chemical handle that can participate in subsequent transformations, enabling controlled introduction of functional motifs onto ornithine-based frameworks. The 3-methylbutyl substituent provides a hydrophobic anchor that can affect solubility and local microenvironment during derivatization and downstream conjugation. The protected amino acid format supports staged deprotection and selective reactions, enabling preparation of modified ornithine derivatives for chemical biology research and synthetic organic chemistry intermediate generation.
3. Chemical Biology Probes
N-α-Fmoc-N-δ-1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)-3-methylbutyl-D-ornithine can be applied to chemical biology probe construction where stereodefined amino acid incorporation is required. The D-configuration and ornithine-derived side-chain topology enable placement of a non-proteinogenic stereochemical element into peptide or peptidomimetic scaffolds, which can be used to probe structure-function relationships in binding and recognition assays without relying on native L-ornithine geometry. The Fmoc-protected α-amino group supports reliable incorporation into labeled or functionalized peptide constructs, while the carbonyl-containing δ-substituent can serve as a reactive motif for further conjugation or reporter attachment strategies. The resulting labeled or derivatized biomolecule analogs can be used as biochemical research intermediates for studying molecular recognition, enzyme tolerance to stereochemical variation, and side-chain effect mapping.
4. Peptidomimetics And SAR Studies
N-α-Fmoc-N-δ-1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)-3-methylbutyl-D-ornithine supports peptidomimetic design and structure-activity relationship exploration by providing a stereodefined ornithine unit with a hydrophobic side chain and a carbonyl-rich substituent. The combination of Fmoc-controlled N-terminal handling and δ-site protection allows systematic variation of side-chain chemistry while maintaining consistent coupling behavior across analog series. The D-ornithine stereochemistry can be leveraged to modulate conformational ensembles and interaction geometries in peptide analogs, enabling SAR studies that distinguish stereochemical contributions from functional group effects. The cyclohexenylidene carbonyl motif can be retained as a structural element or converted into additional functionalities, supporting iterative library synthesis and downstream scaffold diversification in medicinal chemistry and applied peptide science.
5. Pharmaceutical Intermediate Preparation
N-α-Fmoc-N-δ-1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)-3-methylbutyl-D-ornithine is suitable for pharmaceutical intermediate preparation where protected amino acid derivatives are manufactured for downstream peptide or peptidomimetic synthesis. The Fmoc-protected α-amino group and the stable δ-substitution strategy support controlled handling during multistep manufacturing routes, including intermediate storage, purification, and sequential coupling operations. The presence of defined carbonyl functionality within the δ-substituent provides a predictable chemical identity for later transformation into drug-like motifs or for incorporation into active-fragment precursors. The stereochemically defined D-ornithine core aligns with industrial requirements for chiral building blocks, enabling consistent synthesis of stereopure peptide intermediates and supporting fine chemical production pipelines that rely on protected amino acid chemistry.
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