N-α-Fmoc-N-γ-2,4-dintrophenyl-D-2,4-diaminobutyric acid is a protected, non-proteinogenic amino acid derivative featuring a D-configuration and a side chain bearing two amino substituents, one of which is N-γ-arylated with a 2,4-dinitrophenyl group. The molecule contains an Fmoc-protecting group on the α-amino functionality and retains a free carboxyl group, while the 2,4-dinitrophenyl substituent introduces an electron-deficient aromatic moiety suitable for spectroscopic and conjugation-related chemistry. In peptide and amino acid derivative synthesis, it functions as a stepwise-building block that controls chemoselectivity at the α-amino position and provides a defined, masked side-chain handle for structure-activity studies, chemical labeling, or preparation of more complex diamino acid-containing constructs.
CAT No: CP05327
N-α-Fmoc-N-γ-2,4-dintrophenyl-D-2,4-diaminobutyric acid is an Fmoc-protected, chiral amino acid derivative in which the D-2,4-diaminobutyric acid backbone bears an N-γ substituted 2,4-dinitrophenyl group. The molecule contains the Fmoc carbamate on the α-nitrogen, a stereogenic center at the D-configuration, and a strongly electron-withdrawing aromatic dinitrophenyl functionality that modulates the reactivity of the side-chain amino group. The presence of two amino functionalities in a protected/activated arrangement makes the compound suitable for controlled peptide coupling and for downstream chemoselective transformations based on nitroaromatic reactivity and amine deprotection strategies. The aromatic nitro groups also provide spectroscopic handles for analytical research and for building protected intermediates that can be carried through peptide synthesis and later converted into new functional motifs.
1. Peptide Synthesis
N-α-Fmoc-N-γ-2,4-dintrophenyl-D-2,4-diaminobutyric acid is applied in peptide synthesis workflows where an Fmoc-protected amino acid building block is required for stepwise solid-phase or solution-phase coupling. The Fmoc group enables orthogonal N-protection logic, while the D-configuration provides stereochemical control at the amino acid center incorporated into peptide backbones. The N-γ 2,4-dinitrophenyl substitution can function as a side-chain protection/activation element, allowing selective manipulation of the diamino side-chain during peptide assembly and post-coupling diversification. The resulting peptides and peptide fragments derived from this amino acid can be used to generate defined amino acid sequences and to probe how protected diamino side chains influence peptide conformation and reactivity, supporting amino acid chemistry and peptide science development.
2. Chemical Biology Probes
N-α-Fmoc-N-γ-2,4-dintrophenyl-D-2,4-diaminobutyric acid is suitable for chemical biology research that uses nitroaromatic and amine-bearing motifs as tagging or recognition elements within peptide-based probes. The 2,4-dinitrophenyl group provides an electron-deficient aromatic system that can participate in chemoselective transformations and can serve as a built-in analytical reporter during synthesis and characterization. The protected diamino side-chain arrangement supports controlled exposure of amines after deprotection, enabling subsequent conjugation to electrophiles, activated esters, or other functional handles in biomolecule labeling contexts. The D-stereochemistry and the Fmoc-protected α-amino group help maintain structural fidelity when the probe is incorporated into peptide scaffolds for downstream cellular or biochemical assay development.
3. Bioconjugation Chemistry
N-α-Fmoc-N-γ-2,4-dintrophenyl-D-2,4-diaminobutyric acid is used as an intermediate for constructing bioconjugation-ready amino acid derivatives and peptide conjugates. The molecule's amino-rich side chain, combined with the nitroaromatic 2,4-dinitrophenyl group, supports a protection strategy where amine availability can be tuned for sequential conjugation steps. The Fmoc carbamate allows controlled deprotection to generate a reactive N-terminus for coupling to carrier proteins, linkers, or multivalent scaffolds while preserving the integrity of other functional groups. The ability to carry the nitroaromatic functionality through synthesis and then transform it into new reactive or labeled derivatives makes this compound relevant to biomolecule modification and applied peptide conjugate construction in research-grade workflows.
4. Peptidomimetics And SAR Studies
N-α-Fmoc-N-γ-2,4-dintrophenyl-D-2,4-diaminobutyric acid is applied in peptidomimetic design and structure-activity relationship studies where diamino side-chain geometry and stereochemistry are key determinants of molecular recognition. The D-configuration and the defined substitution pattern at the γ-nitrogen help generate consistent stereochemical features in peptide analogs, supporting reproducible SAR campaign libraries. The N-γ 2,4-dinitrophenyl group can act as a handle for controlled side-chain functionalization, enabling conversion to alternative amine-reactive or heteroatom-containing motifs after peptide assembly. The resulting peptidomimetic series can be synthesized with peptide coupling-compatible protection logic, facilitating iterative medicinal chemistry exploration of backbone and side-chain effects using amino acid derivative chemistry.
5. Process Chemistry Intermediate
N-α-Fmoc-N-γ-2,4-dintrophenyl-D-2,4-diaminobutyric acid serves as a chiral amino acid intermediate for process chemistry routes that require robust orthogonal protection and downstream functional-group transformation. The Fmoc-protected α-amino group supports standardized coupling chemistry, while the nitroaromatic 2,4-dinitrophenyl substitution provides a chemically distinct functional region that can be leveraged for later conversion steps in manufacturing of functionalized amino acid derivatives. The presence of a single stereocenter and a defined side-chain substitution pattern supports reproducible batch-to-batch stereochemical outcomes when incorporated into larger peptide or peptidomimetic intermediates. The compound can therefore be employed in specialty chemical production where amino acid ester/amide construction, protected amino acid synthesis, and controlled deprotection/derivatization sequences are integrated into scalable synthetic planning.
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