Boc-D-Dab(2,4-Dnp)-OH is a protected, non-proteinogenic amino acid derivative featuring a Boc-protected amino group and a D-configured Dab (2,4-diaminobutyric acid) backbone bearing a 2,4-dinitrophenyl (Dnp) substituent on the side chain. The molecule contains a Boc carbamate, a free carboxylic acid functional group, and an aromatic 2,4-dinitrophenyl moiety that provides strong electron-withdrawing character and a defined chromophoric/derivatization handle while the stereocenter is specified as D by the product name. In synthesis and chemical biology workflows, it is used as a stepwise building block for preparing labeled or modified peptides and as a substrate or reference material in analytical studies that leverage the Dnp aromatic tag for detection, derivatization control, or structure-reactivity investigations.
CAT No: CP05313
CAS No:1263045-90-4
Synonyms/Alias:N-α-Boc-N-γ-2,4-dintrophenyl-D-2,4-diaminobutyric acid dicyclohexylamine salt;
Boc-D-Dab(2,4-Dnp)-OH is a Boc-protected D-configured amino acid derivative in which the side chain corresponds to D-2,4-diaminobutyric acid (Dab) bearing a 2,4-dinitrophenyl (Dnp) substituent. The molecule contains a tert-butoxycarbonyl (Boc) carbamate on the α-amino group, a free carboxylic acid for C-terminal chemistry, and an aryl Dnp chromophore that introduces strong electron-withdrawing character and a nitro-activated aromatic handle for derivatization and spectroscopic tracking. The D stereocenter at the Dab framework supports stereochemically defined peptide coupling and downstream chiral recognition in synthetic and analytical workflows. The Dnp group can participate in nucleophilic aromatic substitution under appropriate conditions and also enables characteristic UV/visible and MS readouts, making the compound a practical chiral intermediate for protected amino acid synthesis and labeled scaffold construction.
1. Protected Amino Acid Chemistry
Boc-D-Dab(2,4-Dnp)-OH is applied in protected amino acid synthesis and peptide-building-block preparation where Boc carbamate protection enables controlled peptide coupling at the α-amino terminus. The free carboxylic acid supports conversion into activated esters or coupling-ready derivatives, while the D configuration at the Dab center preserves stereochemical integrity through acylation steps. The 2,4-dinitrophenyl substituent provides a stable aromatic tag that can be retained during early coupling chemistry and later used for selective functional transformations or analytical verification. The resulting intermediate can be employed to construct defined peptide segments and chiral amino acid derivatives for synthetic methodology development and structure-defined intermediate generation.
2. Peptide Synthesis Coupling
Boc-D-Dab(2,4-Dnp)-OH is suitable for peptide synthesis workflows that require incorporation of a D-amino acid residue with a side-chain aromatic label. The Boc-protected α-amino group supports standard peptide coupling strategies after deprotection, while the carboxyl functionality enables formation of amide bonds to neighboring residues. The Dnp-tagged side chain can influence local reactivity and steric environment during coupling and can serve as a spectroscopic marker for monitoring resin-bound or solution-phase intermediates. The stereodefined Dab residue supports preparation of D-containing peptides and peptide analogs for mapping stereochemical effects, enabling downstream generation of peptidomimetic scaffolds with traceable side-chain functionality.
3. Chemical Biology Labeling
Boc-D-Dab(2,4-Dnp)-OH is used in chemical biology research contexts where aromatic Dnp labeling facilitates detection and controlled modification of amino acid-derived frameworks. The Dnp chromophore provides strong UV/visible absorbance and characteristic mass signatures, supporting analytical readouts for labeled peptides, conjugates, or reaction intermediates. The Boc protection strategy allows temporal control over amine availability, enabling sequential deprotection and conjugation steps that preserve the D stereocenter. The labeled amino acid derivative can be incorporated into biomolecule-reactive constructs or peptide probes to support molecular recognition studies and side-chain tracking in biochemical assay development.
4. Peptidomimetics And SAR Studies
Boc-D-Dab(2,4-Dnp)-OH supports peptidomimetic construction and structure-activity relationship (SAR) studies by providing a D-configured Dab residue with an aryl Dnp substituent that can modulate electronics and binding interactions. The α-carboxylic acid and Boc-protected amine enable systematic assembly into analog series where stereochemistry and side-chain labeling are held constant while other positions are varied. The nitro-substituted aromatic group can act as a handle for further chemical diversification, including transformations that change polarity or introduce additional functional groups for SAR mapping. The compound therefore functions as a chiral, label-bearing amino acid intermediate for generating defined analog libraries and for correlating structural features with observed physicochemical or binding behavior in research settings.
5. Process Chemistry Intermediate
Boc-D-Dab(2,4-Dnp)-OH is relevant to process chemistry and fine chemical synthesis as a protected amino acid intermediate that combines orthogonal protection (Boc) with a robust aromatic tagging group (Dnp). The Boc carbamate can be managed through controlled deprotection steps to unlock the α-amino functionality for downstream coupling while maintaining the Dnp aromatic moiety during intermediate handling. The presence of a carboxylic acid supports conversion to manufacturing-friendly activated forms for peptide fragment assembly or for preparing larger chiral intermediates. The stereochemically defined Dab framework and stable Dnp label make the compound suitable for reproducible intermediate preparation where analytical traceability and consistent stereochemical outcomes are required in industrial-scale amino acid derivative production.
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