Fmoc-Dap(Dnp)-OH is a protected, non-natural amino acid derivative in which the side chain of 2,3-diaminopropanoic acid (Dap) bears a 2,4-dinitrophenyl (Dnp) substituent, while the alpha-amino group is protected as an Fmoc carbamate. The molecule contains an Fmoc-protected amine, a Dnp-modified side-chain functionality, and a free carboxylic acid group, with the Dnp group providing an aromatic electron-withdrawing tag suitable for spectroscopic and conjugation-oriented studies. In peptide chemistry, this protected analogue is used as a building block for stepwise incorporation of the Dnp-functionalized diamino acid residue into peptides and for preparing labeled peptide or amino-acid derivatives for chemical biology and analytical method development.
CAT No: CP05836
CAS No:140430-54-2
Synonyms/Alias:N-α-Fmoc-N-β-2,4-dinitrophenyl-L-2,3-diaminopropionic acid;140430-54-2;(S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-((2,4-dinitrophenyl)amino)propanoicacid;Fmoc-Dap(Dnp)-OH;AmbotzFAA1463;SCHEMBL6158642;CTK8C5146;MolPort-006-705-613;C24H20N4O8;6825AA;ANW-74345;ZINC38528685;RTR-005252;AJ-95460;AK-61220;AN-31586;FT-0679754;I14-15331;N-beta-2,4-Dinitrophenylfmoc-L-diaminopropionicacid;N-a-Fmoc-N-b-2,4-dinitrophenyl-L-2,3-diaminopropionicacid;N-Fmoc-N'-(2,4-dinitrophenyl)-L-2,3-diaminopropionicacid;(2S)-3-(2,4-dinitroanilino)-2-(9H-fluoren-9-ylmethoxycarbonylamino)propanoicacid;(2S)-3-[(2,4-dinitrophenyl)amino]-2-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}propanoicacid
Fmoc-Dap(Dnp)-OH is a fluorenylmethoxycarbonyl (Fmoc) protected lysine-side-chain analog bearing a Dnp (2,4-dinitrophenyl) group on the side-chain amine, yielding a chiral amino acid derivative suitable for orthogonally protected peptide chemistry. The molecule contains an Fmoc carbamate at the alpha-amino position, a free carboxylic acid for coupling, and a Dnp-activated side-chain functionality that can participate in derivatization and selective deprotection workflows. The presence of the Dnp chromophore and the protected amine arrangement provides a strong spectroscopic handle for tracking, while the stereogenic center supports stereochemically defined incorporation into peptide sequences. The overall reactivity profile is dominated by peptide coupling at the C-terminal carboxyl group and by controlled manipulation of the side-chain amine under conditions compatible with Fmoc removal strategies.
1. Peptide Synthesis
Fmoc-Dap(Dnp)-OH is employed as a protected amino acid building block for solid-phase and solution-phase peptide synthesis where orthogonal protection of the side-chain amine is required. The Fmoc group enables standard base-labile deprotection for N-terminal exposure, while the Dnp-protected side-chain amine supports controlled side-chain chemistry after coupling. The carboxylic acid functionality participates in amide bond formation using common peptide coupling activation modes, allowing incorporation of the Dap(Dnp) residue at defined positions within peptide chains. Downstream peptide analogs can be generated by sequential deprotection and side-chain transformation, supporting structure-activity relationship studies and sequence-specific scaffold construction in amino acid chemistry.
2. Chemical Biology Probes
Fmoc-Dap(Dnp)-OH is suitable for chemical biology workflows that require an amino acid-derived labeling handle and a spectroscopic tag for monitoring incorporation or reaction progress. The Dnp group provides an aromatic, electron-deficient chromophore that can serve as a detectable moiety during derivatization steps and can be leveraged to generate labeled peptide or protein fragments after controlled side-chain amine manipulation. The Fmoc-protected alpha-amine allows clean coupling into peptides or peptide-like conjugates, maintaining compatibility with orthogonal deprotection strategies used in bioconjugation chemistry. The resulting Dap-containing conjugates can function as research reagents for tracking biomolecular interactions, mapping modification sites, and generating defined peptide probes for biochemical investigation.
3. Bioconjugation Chemistry
Fmoc-Dap(Dnp)-OH can be applied in bioconjugation and biomolecule modification programs where a protected lysine-like side chain is needed to control site selectivity. The side-chain amine protected as a Dnp derivative can be transformed into reactive amine-bearing intermediates under conditions that preserve peptide backbone integrity, enabling subsequent conjugation to electrophiles or activated biomolecule scaffolds. The Fmoc group supports stepwise assembly of peptide linkers, facilitating controlled generation of N-terminal and side-chain functionalities for conjugate construction. This amino acid derivative therefore supports the preparation of defined bioconjugates, including peptide-tagged constructs used in protein engineering, analytical research, and molecular recognition studies.
4. Peptidomimetics And SAR
Fmoc-Dap(Dnp)-OH is utilized in peptidomimetic and medicinal chemistry-oriented synthesis where a stereodefined, lysine-side-chain mimic is incorporated to probe binding determinants. The Dap(Dnp) side-chain architecture provides a handle for installing functional groups that influence charge distribution, hydrogen-bonding patterns, and local conformational preferences in peptide analogs. The protected amine arrangement enables systematic variation of side-chain chemistry through sequential deprotection and derivatization, supporting structure-activity relationship studies on receptor-binding motifs or enzyme recognition elements. The Fmoc-enabled coupling compatibility also supports rapid generation of analog libraries on a defined synthetic platform for downstream SAR evaluation.
5. Process Chemistry Intermediate
Fmoc-Dap(Dnp)-OH serves as a chiral, protected amino acid intermediate for process chemistry and fine chemical synthesis routes that require orthogonal protection to manage multi-functional reactivity. The Fmoc carbamate and Dnp-protected side-chain amine provide chemically distinct functional domains, enabling stepwise manufacturing sequences where peptide coupling and later side-chain transformations can be scheduled without premature cross-reactivity. The free carboxylic acid supports conversion to activated esters or coupling-ready derivatives under controlled conditions, aligning with scalable peptide-building-block manufacturing practices. The Dnp chromophore can also function as an analytical tag during intermediate handling, supporting in-process characterization and consistent downstream conversion to peptide or peptidomimetic targets.
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