Fmoc-Lys(ivDde)-OH is a protected lysine derivative bearing an Fmoc (9-fluorenylmethoxycarbonyl) group on the α-amino functionality and an ivDde (1-(4,4-dimethyl-2,6-dioxocyclohexylidene)ethylidene) protecting group on the ε-amino side chain, classifying it as a stepwise peptide-synthesis building block based on the lysine scaffold. The molecule contains a free carboxylic acid (-COOH) and a stereogenic center consistent with lysine's amino acid framework, while the side-chain ε-amino is masked as a removable acylidene-type protecting group that modulates chemoselectivity during sequential coupling. Fmoc-Lys(ivDde)-OH is employed in solid-phase or solution-phase peptide synthesis workflows to enable controlled orthogonal deprotection of the lysine side chain for subsequent functionalization or incorporation into peptides with defined ε-substitution patterns.
CAT No: CP01445
CAS No:204777-78-6
Synonyms/Alias:N-α-Fmoc-N-ε-1-(4,4-dimethyl-2,6-dioxocyclohex-1 -ylidene)-3-methylbutyl-L-lysine;204777-78-6;Fmoc-Lys(Ddiv)-OH;Fmoc-Lys(IvDde)-OH;(S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-6-((1-(4,4-dimethyl-2,6-dioxocyclohexylidene)-3-methylbutyl)amino)hexanoicacid;N-Fmoc-N'-[1-(4,4-Dimethyl-2,6-dioxocyclohex-1-ylidene)-3-methylbutyl]-L-lysine;C34H42N2O6;Nalpha-Fmoc-Nepsilon-[1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)-3-methylbutyl]-L-lysine;Fmoc-L-Lys(Ivdde)-OH;29207_ALDRICH;SCHEMBL178768;29207_FLUKA;CTK1A1512;MolPort-003-929-341;AKOS015837177;AKOS015895471;ZINC100008472;RTR-009555;AK-49549;SC-09710;AB0044327;A7927;ST51052987;Y3453;I06-1184;N|A-Fmoc-N|A-[1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)-3-methylbutyl]-L-lysine
Fmoc-Lys(ivDde)-OH is a protected lysine derivative bearing an N-(9H-fluoren-9-ylmethoxycarbonyl) (Fmoc) group and a side-chain amine protected as an ivDde carbamate, retaining the lysine α-amino acid backbone for peptide coupling. The molecule contains a stereogenic center at the α-carbon (lysine configuration) and presents orthogonal protecting-group logic: the Fmoc group can be removed under base for standard solid-phase peptide synthesis, while the ivDde group can be selectively cleaved under conditions compatible with preserved peptide integrity. The carboxylic acid is present as a free acid for activation to peptide bonds, and the side-chain functionality is masked to prevent premature amide formation. This orthogonally protected, chiral amino acid derivative functions as a controlled intermediate for constructing lysine-containing sequences and for introducing side-chain modifications at defined stages of synthesis.
1. Peptide Synthesis
Fmoc-Lys(ivDde)-OH serves as a lysine building block for automated peptide assembly, where the Fmoc-protected α-amine supports iterative N-terminal deprotection and coupling cycles. The free carboxylic acid enables formation of amide bonds to the growing peptide chain, while the ivDde-protected ε-amine suppresses side reactions during chain elongation. Orthogonality between Fmoc and ivDde protecting groups allows selective side-chain unmasking at a later synthesis step, enabling targeted lysine functionalization without scrambling protecting-group patterns. Downstream peptide analogs prepared from this intermediate are suitable for generating defined lysine motifs in research-grade peptide libraries and process-compatible manufacturing workflows.
2. Side-Chain Functionalization
Fmoc-Lys(ivDde)-OH supports programmed lysine side-chain chemistry by deferring ε-amine exposure until after peptide backbone construction. The ivDde carbamate protection strategy provides a controlled handle for subsequent derivatization, including formation of urea, amide, sulfonamide, or carbamate linkages depending on the electrophile employed in later steps. The presence of the stable Fmoc group during early coupling stages helps maintain peptide fidelity, while selective ivDde removal enables site-selective conjugation at a single lysine position. Resulting side-chain-modified peptides and peptidomimetics can be used to probe molecular recognition, tune physicochemical properties, or generate conjugation-ready scaffolds for biochemical research.
3. Bioconjugation Chemistry
Fmoc-Lys(ivDde)-OH is applicable to bioconjugation workflows that require controlled installation of functional groups onto lysine residues within peptide constructs. The orthogonally protected ε-amine minimizes off-target coupling during peptide synthesis, and the later unmasking of the lysine side chain can be used to generate attachment points for linkers, affinity tags, or labeling reagents. The combination of an Fmoc backbone for peptide assembly and an ivDde-protected side chain aligns with strategies that aim to preserve defined conjugation stoichiometry and positional accuracy. Bioconjugate intermediates derived from this amino acid derivative can be advanced into chemical biology studies and analytical reference materials where lysine-specific labeling is required.
4. Peptidomimetics And SAR Studies
Fmoc-Lys(ivDde)-OH enables the construction of lysine-containing peptidomimetics used in structure-activity relationship studies and molecular scaffold optimization. The protected lysine side chain allows incorporation of amino acid analogs bearing defined ε-substituents, supporting systematic variation of charge distribution, hydrogen-bonding capacity, and steric environment at the lysine position. The chiral α-amino acid stereocenter and controlled functional-group presentation help maintain consistent backbone geometry across analog series. Synthesized analogs can be utilized as SAR probes to correlate side-chain modifications with binding or reactivity patterns in biochemical screening and mechanistic investigations.
5. Pharmaceutical Manufacturing Intermediates
Fmoc-Lys(ivDde)-OH can be employed as a manufacturing-oriented intermediate for producing lysine-rich peptide intermediates used in industrial peptide synthesis supply chains. The orthogonal protecting-group design supports scalable process planning by allowing stepwise deprotection and selective side-chain derivatization while maintaining compatibility with standard peptide coupling technologies. The presence of a free carboxylic acid facilitates activation routes to peptide bonds, and the protected ε-amine reduces the likelihood of undesired branching or crosslinking during upstream processing. Industrially produced peptide building blocks and protected intermediates derived from this compound can feed downstream synthesis of defined peptide products for research and specialty chemical applications.
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