Fmoc-L-Lys(Dnp)-OH

Fmoc-L-Lys(Dnp)-OH is an Fmoc-protected lysine derivative bearing a side-chain Dnp substituent, combining a chiral α-amino acid backbone with a nucleophilic ε-amino group that has been derivatized as a 2,4-dinitrophenyl (Dnp) adduct. The molecule contains the Fmoc carbamate on the α-nitrogen, a free carboxylic acid for peptide coupling, and a strongly electron-withdrawing aromatic Dnp group on the lysine side chain that modulates basicity and reactivity of the ε-amino functionality. The chiral stereocenter at the α-carbon is retained as L-configuration, supporting stereochemically defined peptide assembly and downstream manipulations of lysine side-chain chemistry. The Dnp moiety provides a characteristic spectroscopic and derivatization handle while also enabling controlled deprotection or substitution strategies to generate lysine-like functionality or specialized tagged intermediates.

1. Peptide Synthesis

Fmoc-L-Lys(Dnp)-OH serves as a protected lysine building block for solid-phase peptide synthesis and related peptide assembly workflows where side-chain functionality must be masked during chain elongation. The Fmoc group supports standard N-terminal protection and base-labile deprotection to expose the α-amino group for coupling, while the Dnp-protected ε-amino substituent reduces undesired side reactions during peptide bond formation. The presence of a free carboxylic acid enables amide coupling to growing peptide chains, and the defined L-configuration ensures stereochemical fidelity at the lysine residue. Lysine incorporation with a Dnp side-chain tag can be applied to peptide synthesis that requires later side-chain conversion, selective labeling, or analytical traceability of the lysine position in the final construct.

2. Chemical Biology Labeling

Fmoc-L-Lys(Dnp)-OH can be used in chemical biology and biomolecular labeling strategies that exploit the Dnp aromatic tag for controlled detection and selective functional transformations. The lysine scaffold provides an ε-amino-derived attachment point that is temporally protected as a Dnp adduct, enabling stepwise modification workflows where labeling or side-chain conversion is deferred until after peptide or conjugate assembly. The Fmoc-protected α-amino functionality supports incorporation into peptide-based probes, while the Dnp group introduces a chromophoric motif that may facilitate monitoring of intermediate stages and positional assignment in lysine-containing biomolecules. Downstream conjugate formation can leverage the lysine-derived connectivity after Dnp handling, supporting generation of labeled peptides, affinity reagents, or mapping probes for biochemical studies.

3. Peptidomimetics And SAR

Fmoc-L-Lys(Dnp)-OH supports peptidomimetic construction and structure-activity relationship studies by enabling lysine side-chain patterning with a defined aromatic substituent. The protected amino acid format allows incorporation into peptide analogs where the ε-amino group is intentionally modified to tune polarity, hydrogen-bonding, and local sterics relative to native lysine. The Dnp moiety can function as a removable or transformable handle, allowing iterative design cycles where analogs are synthesized with controlled side-chain chemistry and subsequently converted to alternative lysine-like functionalities. The resulting analog series can be applied to SAR investigations that depend on precise stereochemistry at the α-carbon and controlled side-chain reactivity during synthetic diversification.

4. Protected Amino Acid Chemistry

Fmoc-L-Lys(Dnp)-OH functions as a chiral, orthogonally protected lysine derivative for protected amino acid synthesis and intermediate preparation in fine chemical manufacturing contexts. The Fmoc carbamate provides a widely used orthogonal protection element for the α-amino group, while the Dnp adduct on the ε-amino group introduces a distinct protection and derivatization regime that can be addressed under compatible conditions in multistep sequences. The combination of a base-labile N-protecting group and an aromatic Dnp side-chain handle enables route design in which selective deprotection, substitution, or conversion of the lysine side chain can be scheduled at defined steps. The free carboxylic acid supports coupling chemistry, making the compound suitable for producing lysine-containing intermediates, peptide building blocks, and downstream derivatives that require controlled functional-group exposure.

5. Analytical Research Standards

Fmoc-L-Lys(Dnp)-OH can be applied to analytical research and method development where Dnp-tagged lysine residues provide a characteristic chemical signature for tracking and identification. The Dnp aromatic group contributes strong UV-visible absorbance characteristics and can aid in monitoring derivatization states of lysine-containing intermediates, while the Fmoc-protected backbone supports reproducible handling during synthetic workflows. The defined structure, including L-stereochemistry and a single lysine side-chain modification pattern, makes the compound suitable as a reference material for LC-MS/MS method validation, peptide mapping standards, and characterization of lysine incorporation in synthetic libraries. Downstream use can include supporting analytical workflows that distinguish protected versus converted lysine side-chain forms in peptide and peptidomimetic synthesis pipelines.

1. Emu oil in combination with other active ingredients for treating skin imperfections

2. Spatiotemporal delivery of nanoformulated liraglutide for cardiac regeneration after myocardial infarction

3. Cationic cell-penetrating peptides are potent furin inhibitors

4. Myotropic activity of allatostatins in tenebrionid beetles

5. Autoinhibition and phosphorylation-induced activation of phospholipase C-γ isozymes