N-α-Fmoc-N-γ-2,4-dintrophenyl-L-2,4-diaminobutyric acid is a protected, non-proteinogenic amino acid derivative featuring a 2,4-diaminobutyric acid backbone bearing an N-α Fmoc protecting group and an N-γ 2,4-dintrophenyl substituent. The molecule contains an amino acid α-amino group and a carboxyl group, while its side chain presents two amino functionalities with one nitrogen masked as a 2,4-dintrophenyl aromatic carbamate-like protecting/derivatizing group, and the stereochemistry is specified as L at the α-carbon. In peptide and amino acid chemistry workflows, the Fmoc group supports stepwise assembly on solid supports, whereas the 2,4-dintrophenyl substitution provides a protected functional handle for controlling chemoselectivity and enabling downstream transformations or conjugation/labeling strategies involving the remaining amino functionality.
CAT No: CP05328
N-α-Fmoc-N-γ-2,4-dintrophenyl-L-2,4-diaminobutyric acid is an Fmoc-protected, chiral amino acid derivative featuring an α-amino group masked as an N-Fmoc carbamate and a side chain bearing a 2,4-dinitrophenyl-protected amino functionality. The molecule contains the amino acid backbone with a stereogenic center at the L-configuration, a carboxylic acid handle suitable for peptide coupling after activation, and an aromatic dinitrophenyl group that functions as an electron-withdrawing protecting motif for the side-chain amine. The presence of the Fmoc group enables standard base-labile deprotection to reveal the α-amine during stepwise solid-phase or solution-phase peptide assembly, while the dinitrophenyl group can be removed under conditions compatible with downstream functional group tolerance. The combined protecting-group pattern supports controlled orthogonality between backbone and side-chain reactivity, making the compound a research-grade intermediate for constructing amino acid sequences and functionalized peptide analogs with defined chemoselectivity.
1. Peptide Synthesis
N-α-Fmoc-N-γ-2,4-dintrophenyl-L-2,4-diaminobutyric acid is used as a protected peptide building block in peptide synthesis workflows that require orthogonal protection of both the α-amino functionality and a side-chain amine. The Fmoc carbamate supports iterative peptide coupling by providing an inert α-nitrogen during activation of the carboxyl group, then enabling base-triggered Fmoc removal to generate a reactive amine for subsequent coupling cycles. The side-chain 2,4-dinitrophenyl group reduces premature amide formation by masking the additional amino site, allowing controlled incorporation of the diamino acid motif into peptide frameworks. The resulting protected diamino acid residue can be carried forward into peptide analog construction and can be further transformed after peptide assembly to expose or derivatize the side-chain amine for functional studies.
2. Chemical Biology Probes
N-α-Fmoc-N-γ-2,4-dintrophenyl-L-2,4-diaminobutyric acid is applicable to chemical biology research where masked amines are needed to tune reactivity during probe synthesis and subsequent activation. The dinitrophenyl-protected side-chain amine provides a stable aromatic handle that can participate in selective deprotection or serve as a chemical trigger enabling generation of a free diamino motif in later synthetic stages. The Fmoc-protected backbone supports incorporation into peptide conjugates that can be processed into imaging, affinity, or binding probes after controlled unmasking of the side-chain functionality. The compound's defined stereochemistry and protected functional groups enable systematic structure-function evaluation of peptide-based chemical probes and related molecular recognition reagents.
3. Side-Chain Functionalization
N-α-Fmoc-N-γ-2,4-dintrophenyl-L-2,4-diaminobutyric acid supports side-chain functionalization strategies that rely on orthogonal amine protection for sequential derivatization. The diamino acid framework contains two nitrogen sites whose reactivity can be modulated by the Fmoc group on the α-amino position and the 2,4-dinitrophenyl protection on the γ-amino position. The carboxylic acid enables formation of amide linkages to install the residue into larger scaffolds, while the masked side-chain amine can be converted into downstream functional groups after deprotection, such as attachment points for crosslinkers, conjugation handles, or further protected intermediates. The compound therefore functions as a controlled intermediate for generating amino acid derivatives and peptide analogs bearing defined numbers and positions of reactive amines.
4. Chiral Amino Acid Intermediate
N-α-Fmoc-N-γ-2,4-dintrophenyl-L-2,4-diaminobutyric acid serves as a chiral amino acid intermediate for stereoselective synthesis of functionalized peptide fragments and related chiral building blocks. The L-configuration at the α-carbon provides a fixed stereochemical element that can influence conformational preferences in peptide chains and can be propagated through coupling steps to maintain stereochemical integrity in downstream derivatives. The Fmoc-protected α-amino group and the protected side-chain amine establish a predictable reactivity profile that is compatible with standard peptide coupling chemistry and orthogonal deprotection sequences. The compound can be employed to prepare chiral intermediates for SAR-oriented studies, fragment-based molecular design, and method development in amino acid derivatization and peptide construction.
5. Pharmaceutical Manufacturing
N-α-Fmoc-N-γ-2,4-dintrophenyl-L-2,4-diaminobutyric acid is suitable for manufacturing-oriented peptide intermediate preparation where controlled protection of amines supports scalable peptide synthesis routes. The Fmoc group enables reliable protection of the α-amino functionality during repeated coupling operations, while the dinitrophenyl-protected side-chain amine can help manage chemoselectivity when producing peptide sequences containing additional nucleophilic sites. The presence of a carboxylic acid for activation and coupling allows integration into automated or semi-automated peptide assembly strategies, supporting consistent formation of amide bonds under defined process conditions. The compound's orthogonality between backbone and side-chain nitrogen reactivity can facilitate downstream deprotection and conversion steps used to generate functional peptide intermediates for further chemical modification and final product assembly in industrial fine chemical production.
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