Dde-Lys(Fmoc)-OH is an Fmoc-protected lysine derivative in which the ε-amino group of lysine is masked with a Dde (1-(4,4-dimethyl-2,6-dioxocyclohexylidene)ethyl) protecting group while the α-carboxyl group remains present as a free carboxylic acid and the α-amino group is protected as the Fmoc carbamate. The molecule therefore contains both an Fmoc-protected α-amino functionality and a Dde-protected side-chain amine, with the lysine backbone providing a (CH2)4 side chain terminating in the protected ε-nitrogen. In peptide synthesis workflows, this protected amino acid is used as a building block for stepwise assembly where orthogonal deprotection of the Dde group can expose the ε-amino side chain without removing the Fmoc group, supporting controlled formation of side-chain-substituted lysine residues and related peptide intermediates.
CAT No: CP01433
CAS No:156648-40-7
Synonyms/Alias:N-α-1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)ethyl-N-ε-Fmoc-L-lysine;Dde-Lys(Fmoc)-OH;156648-40-7;L-Lysine, N2-[1-(4,4-dimethyl-2,6-dioxocyclohexylidene)ethyl]-N6-[(9H-fluoren-9-ylmethoxy)carbonyl]-;(2S)-6-(9H-fluoren-9-ylmethoxycarbonylamino)-2-[1-(2-hydroxy-4,4-dimethyl-6-oxocyclohexen-1-yl)ethylideneamino]hexanoic acid;dde-l-lys(fmoc)-oh;MFCD00467662;N6-(((9H-Fluoren-9-yl)methoxy)carbonyl)-N2-(1-(4,4-dimethyl-2,6-dioxocyclohexylidene)ethyl)-L-lysine;(2S)-2-[1-(4,4-dimethyl-2,6-dioxocyclohexylidene)ethylamino]-6-(9H-fluoren-9-ylmethoxycarbonylamino)hexanoic acid;(2S)-2-{[1-(4,4-DIMETHYL-2,6-DIOXOCYCLOHEXYLIDENE)ETHYL]AMINO}-6-{[(9H-FLUOREN-9-YLMETHOXY)CARBONYL]AMINO}HEXANOIC ACID;L-Lysine, N2-(1-(4,4-dimethyl-2,6-dioxocyclohexylidene)ethyl)-N6-((9H-fluoren-9-ylmethoxy)carbonyl)-;n-alpha-1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)ethyl-n-epsilon-fmoc-l-lysine;SCHEMBL3502087;DTXSID80679793;HJGADLBSAXYSSH-VWLOTQADSA-N;XH1414;AKOS015911819;DS-15038;CS-0137316;F10658;N^a-1-(4,4-Dimethyl-2,6-dioxocyclohex-1-ylidene)ethyl-N^e-Fmoc-L-lysine;N-alpha-(4,4-Dimethyl-2,6-dioxocyclohex-1-ylidene)ethyl-N-epsilon-(9-Fmoc)-L-lysine;(S)-6-(((9H-fluoren-9-yl)methoxy)carbonylamino)-2-(1-(4,4-dimethyl-2,6-dioxocyclohexylidene)ethylamino)hexanoic acid;812-215-4;N~2~-[1-(4,4-Dimethyl-2,6-dioxocyclohexylidene)ethyl]-N~6~-{[(9H-fluoren-9-yl)methoxy]carbonyl}-L-lysine;
Dde-Lys(Fmoc)-OH is a lysine derivative bearing an Nα-(Fmoc) protecting group and an additional side-chain amine protected as a Dde (1-(4,4-dimethyl-2,6-dioxocyclohexylidene)ethyl) carbamate, with the free carboxylic acid retained for coupling chemistry. The molecule contains a stereogenic center at the lysine α-carbon, and its protected side chain provides orthogonal deprotection behavior compatible with stepwise peptide assembly. The Fmoc group supports base-labile N-terminal unmasking, while the Dde group is acid-labile, enabling controlled exposure of the ε-amine for selective functionalization. The combination of protected amine functionality, a carboxylic acid handle, and the chiral amino acid backbone makes Dde-Lys(Fmoc)-OH a practical protected amino acid building block for peptide synthesis, side-chain modification, and downstream intermediate formation.
1. Peptide Synthesis
Dde-Lys(Fmoc)-OH is applied in solid-phase peptide synthesis where orthogonally protected lysine is required for sequential N-terminal and side-chain chemistry. The Fmoc-protected α-amine participates in standard peptide coupling after Fmoc removal, while the Dde-protected ε-amine remains masked through multiple coupling cycles. Acid-triggered Dde removal can then generate a reactive lysine side-chain amine for subsequent peptide elongation, branching, or incorporation of tailored functional groups. The free carboxylic acid and protected amine pattern support reliable incorporation into peptide building block sequences used to generate lysine-containing peptides and peptide analogs for biochemical research.
2. Side-Chain Functionalization
Dde-Lys(Fmoc)-OH is used for side-chain functionalization strategies in chemical biology and synthetic organic chemistry, leveraging the orthogonal Dde and Fmoc protecting-group logic. The ε-amine revealed after Dde deprotection can undergo derivatization reactions such as acylation, sulfonylation, carbamate formation, or nucleophilic substitution-based conjugation routes, enabling controlled installation of functional moieties on the lysine side chain. The preserved stereochemistry at the α-carbon helps maintain consistent peptide-like geometry and amide connectivity in downstream derivatives. Side-chain modified products derived from Dde-Lys(Fmoc)-OH can serve as intermediates for peptidomimetics, affinity reagents, and structure-defined conjugation scaffolds.
3. Bioconjugation Chemistry
Dde-Lys(Fmoc)-OH is suitable for bioconjugation workflows where lysine ε-amine chemistry is needed with orthogonal protection to manage multi-step coupling and labeling. The Dde-protected ε-amine can be selectively unmasked under conditions that do not disrupt the Fmoc-protected α-amine during earlier stages of synthesis, allowing staged introduction of reactive handles. The resulting lysine-based amine can be converted into conjugation-ready groups, including activated esters, amide-forming electrophiles, or linkers designed for controlled attachment to biomolecules. The protected amino acid backbone also supports preparation of defined peptide conjugates used in biochemical research intermediate generation and molecular labeling studies.
4. Peptidomimetics And SAR
Dde-Lys(Fmoc)-OH is applied in peptidomimetic construction and structure-activity relationship studies where lysine side-chain positioning influences binding, solubility, and receptor interaction patterns. The protected ε-amine allows systematic variation of side-chain substituents while maintaining a consistent α-amino acid stereochemical framework and peptide-compatible amide connectivity. Dde deprotection followed by controlled derivatization enables generation of libraries of lysine analogs that differ in charge distribution, hydrogen-bonding capacity, and steric environment. The Fmoc-controlled N-terminal handling further supports reproducible synthesis of analog series used as chemical probes and SAR-focused molecular design inputs.
5. Pharmaceutical Manufacturing Intermediates
Dde-Lys(Fmoc)-OH can be employed as a protected amino acid intermediate in manufacturing-oriented peptide and peptide-like intermediate production, where orthogonally protected lysine residues are required for reproducible stepwise assembly. The Fmoc group provides a standardized, base-labile handle for N-terminal deprotection during controlled synthesis sequences, while the Dde group enables selective side-chain amine unmasking for subsequent coupling or functional-group installation. The presence of a free carboxylic acid supports conversion into activated coupling forms under process-compatible conditions, aligning with industrial peptide building block preparation practices. Downstream derivatives prepared from Dde-Lys(Fmoc)-OH can feed into defined intermediate streams for specialty chemical production and fine chemical synthesis of lysine-containing peptide components.
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