N-α -Fmoc-N-β-1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)ethyl-L-2,3-diaminopropionic acid is an Fmoc-protected, amino acid-derived building block featuring an L-2,3-diaminopropionic acid core and a substituted N-β side chain bearing a 4,4-dimethyl-2,6-dioxocyclohex-1-ylidene (cyclohexane-dione/ylidene) functionality. The molecule contains the Fmoc carbamate protecting group on the α-amino nitrogen, a free carboxyl group on the amino acid framework, and additional amino functionality consistent with a diamino-propionic acid motif, with stereochemistry specified at the L-configuration for the amino acid core. In peptide synthesis and related chemical biology workflows, the Fmoc protection supports stepwise assembly by controlling chemoselectivity at the α-amino position, while the N-β appended cyclohexane-dione/ylidene moiety provides a defined, reactive structural handle for constructing more complex amino acid and peptide derivatives.
CAT No: CP05834
N-α -Fmoc-N-β-1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)ethyl-L-2,3-diaminopropionic acid is an Fmoc-protected amino acid derivative featuring an L-configuration at the 2,3-diaminopropionic acid core and an additional β-amino substituent. The molecule contains an Fmoc carbamate for orthogonal N-protection during solid-phase peptide synthesis, along with a side-chain amidine-like arrangement created by the 1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)ethylidene functionality, which provides a defined electrophilic/condensation-reactive motif. Two carbonyl groups within the cyclohexane-1,3-dione-derived ring system contribute strong conjugation and predictable reactivity under nucleophilic and base-mediated conditions, while the diamino framework supports selective derivatization and downstream conversion to peptide-linked or heterocycle-containing analogs. The compound's protected amine and controlled functional-group presentation make it a chiral, peptide-compatible intermediate for constructing amino-acid-derived scaffolds and for preparing defined functionalized residues for biochemical and materials-oriented synthesis.
1. Peptide Synthesis
N-α -Fmoc-N-β-1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)ethyl-L-2,3-diaminopropionic acid serves as an Fmoc-based peptide building block for stepwise assembly on solid supports, where the Fmoc group enables base-labile deprotection and subsequent coupling at the α-amino terminus. The L-2,3-diaminopropionic acid core provides a stereodefined backbone that can be incorporated into peptides to introduce constrained, side-chain functional density. The 1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)ethylidene motif can participate in post-coupling transformations or remain as a functional handle for scaffold diversification after peptide chain elongation. The resulting peptide products can be used to probe sequence-dependent recognition, generate peptidomimetic residues, and support synthetic workflows that require orthogonal protection and controlled side-chain reactivity.
2. Peptidomimetics
N-α -Fmoc-N-β-1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)ethyl-L-2,3-diaminopropionic acid functions in peptidomimetic construction by embedding a stereodefined diamino-containing residue into peptide-like frameworks. The protected N-terminus and the side-chain carbonyl-rich cyclohexanedione-derived unit allow the design of constrained analogs that can undergo further derivatization, including nucleophile-driven modifications and heterocycle-forming pathways. The presence of multiple amine sites supports selective chemical programming, enabling generation of analog series for structure-activity relationship studies focused on backbone rigidity and side-chain electrophilicity. Downstream, the residue can be used to prepare functionalized peptide mimics that serve as chemical biology probes or as intermediate platforms for larger scaffold assembly.
3. Chemical Biology Probes
N-α -Fmoc-N-β-1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)ethyl-L-2,3-diaminopropionic acid can be applied in chemical biology research as a residue-bearing intermediate for making labeled or reactive peptide conjugates. The diaminopropionic acid architecture provides multiple functional sites for controlled conjugation chemistry, while the cyclohexanedione-derived electrophilic motif can enable selective capture or covalent labeling strategies when incorporated into a peptide context. The Fmoc-protected amino group supports clean incorporation into longer sequences, allowing the probe to be positioned at defined locations within a molecular scaffold. Resulting conjugates may be used for studying biomolecular interactions, mapping binding interfaces, or generating defined reactive analogs for mechanistic investigations in protein and nucleic-acid related systems.
4. Process Chemistry Intermediate
N-α -Fmoc-N-β-1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)ethyl-L-2,3-diaminopropionic acid is suitable for process chemistry as a protected chiral intermediate that can be manufactured and handled with protection-group logic aligned to peptide synthesis conditions. The Fmoc carbamate provides a robust N-protection strategy that withstands common coupling environments and can be removed under controlled base exposure, supporting scalable preparation of peptide building blocks and protected amino acid derivatives. The cyclohexane-1,3-dione-derived substituent introduces carbonyl functionality that can be treated as a stable, structurally defined handle during intermediate storage and subsequent downstream transformations. Industrially, the compound can be employed in fine chemical synthesis workflows where stereochemical consistency, orthogonal protection behavior, and predictable functional-group reactivity are required for reliable production of functional peptide analogs and related heterocycle-containing products.
5. Heterocycle-Enabled Synthesis
N-α -Fmoc-N-β-1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)ethyl-L-2,3-diaminopropionic acid enables heterocycle-enabled synthesis by providing a carbonyl-rich, conjugated side-chain motif coupled to a stereodefined amino acid framework. The 2,6-dioxocyclohex-1-ylidene functionality can serve as a reactive precursor for constructing nitrogen-containing ring systems when paired with nucleophiles or intramolecular cyclization strategies after peptide incorporation or during intermediate conversion. The protected amine arrangement supports staged functional group exposure, allowing selective deprotection and controlled engagement of the diamino functionality in subsequent ring-formation steps. The resulting heterocycle-containing amino acid derivatives and peptide-linked analogs can be used for building libraries of constrained scaffolds, generating SAR-focused series, and producing downstream chemical intermediates for specialty chemical manufacturing.
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