N-α-Boc-N-im-dinitrophenyl-L-histidine is a protected L-histidine derivative in which the α-amino group is Boc-protected and the imidazole nitrogen is substituted with a dinitrophenyl group, yielding an amino acid bearing both a protected amine and an aromatic, electron-withdrawing side-chain modification. The molecule contains a free carboxyl functional group and a Boc carbamate on the α-nitrogen, while the imidazole ring bears the N-im dinitrophenyl substituent that changes side-chain polarity and provides a strongly chromophoric aromatic handle. As a chemically defined histidine analogue, it is used as a substrate or building block in peptide-related synthesis and chemical biology workflows, including preparing functionalized peptide intermediates and performing structure-activity or labeling studies that rely on the dinitrophenyl-modified imidazole functionality.
CAT No: CP01008
CAS No:25024-53-7
Synonyms/Alias:Boc-His(Dnp)-OH;25024-53-7;ST067128;Nalpha-Boc-N(im)-2,4-dinitrophenyl-L-histidine;(2S)-2-[(TERT-BUTOXYCARBONYL)AMINO]-3-[1-(2,4-DINITROPHENYL)IMIDAZOL-4-YL]PROPANOICACID;EINECS246-569-0;PubChem18935;AC1L3KIL;15287_ALDRICH;SCHEMBL7284653;L-Histidine,N-((1,1-dimethylethoxy)carbonyl)-1-(2,4-dinitrophenyl)-;15287_FLUKA;MolPort-003-926-738;C17H19N5O8;ACT06561;ZINC2539568;CB-081;AKOS015908391;AKOS015924153;AJ-38893;AK-49605;AM000302;AM039728;SC-09580;FT-0638486
N-α-Boc-N-im-dinitrophenyl-L-histidine is a protected L-histidine derivative featuring the canonical imidazole-containing amino acid side chain and a stereogenic α-carbon in the L-configuration. The molecule bears an N-α Boc protecting group on the amino functionality and an N-im dinitrophenyl (dinitrophenylated imidazole nitrogen) motif that introduces a strongly electron-withdrawing aromatic system and additional chromophoric/UV-active character. The combination of Boc protection and dinitrophenyl substitution modulates nucleophilicity of the imidazole, enabling controlled reactivity during peptide coupling and subsequent functional-group transformations. The resulting protected amino acid intermediate can participate in protected amino acid synthesis workflows where selective deprotection and side-chain unmasking are required for downstream peptide building block preparation and analytical traceability.
1. Protected Amino Acid Synthesis
N-α-Boc-N-im-dinitrophenyl-L-histidine is applied in protected amino acid synthesis and peptide building block preparation where orthogonal protection of the histidine side chain is needed. The Boc-protected α-amino group supports standard peptide coupling chemistry, while the N-im dinitrophenyl imidazole protection reduces side-chain participation and helps maintain chemoselectivity during chain assembly. Controlled deprotection strategies can be used to remove the Boc group and later unmask the histidine imidazole for further coupling or functionalization, aligning with protected amino acid synthesis intermediate design. Downstream use commonly includes conversion into activated derivatives for peptide construction and preparation of histidine-containing sequences for biochemical research and process-oriented fine chemical synthesis.
2. Peptide Synthesis
N-α-Boc-N-im-dinitrophenyl-L-histidine serves as a histidine-compatible residue for peptide synthesis workflows that require side-chain protection compatible with iterative coupling. The imidazole N-substitution by the dinitrophenyl group suppresses undesired side reactions and supports predictable incorporation of the L-histidine stereocenter into growing peptide chains. Boc protection at the α-amino terminus enables sequential N-terminal deprotection/coupling cycles, supporting peptide coupling chemistry for both linear peptides and protected peptide fragments. The chromophoric dinitrophenyl functionality can also facilitate monitoring of intermediate stages in synthetic sequences, supporting robust peptide building block preparation in research and specialty chemical manufacturing.
3. Chemical Biology Probes
N-α-Boc-N-im-dinitrophenyl-L-histidine is suitable for chemical biology research contexts where histidine side-chain chemistry and labeling-compatible handles are required. The protected imidazole nitrogen and the dinitrophenyl aromatic system provide a defined electronic environment that can be leveraged for controlled unmasking and subsequent conjugation steps to generate histidine-bearing probes. Boc protection supports handling stability during derivatization, while the L-configuration preserves stereochemical fidelity relevant to amino acid recognition in biochemical assays. Downstream derivatives can be used to build histidine-containing molecular probes for studying protein-ligand interactions, metal-binding motifs, or amino acid-specific binding events in applied biochemical research.
4. Peptidomimetics And SAR
N-α-Boc-N-im-dinitrophenyl-L-histidine is applied in peptidomimetics and structure-activity relationship studies where histidine-like functionality must be introduced with controlled protection states. The imidazole-bearing side chain, protected as an N-im dinitrophenyl derivative, can function as a staging intermediate for generating analogs with tuned basicity, hydrogen-bonding patterns, or metal-coordination behavior. Boc-protected α-amino chemistry supports incorporation into constrained scaffolds or fragment-based assemblies that require predictable amide formation. Resulting histidine-containing intermediates can be advanced into SAR-focused libraries of peptide analogs and synthetic organic chemistry intermediates used for mechanistic probing and molecular design.
5. Analytical Research Standards
N-α-Boc-N-im-dinitrophenyl-L-histidine is useful in analytical research as a characterized protected amino acid standard and intermediate for method development. The dinitrophenyl group provides strong UV/visible detectability and can support trace monitoring of derivatization, deprotection, and coupling stages in amino acid and peptide workflows. Boc protection and the defined L-stereochemistry help ensure reproducible chromatographic and mass spectrometric behavior for analytical method validation and impurity tracking. Downstream, the compound can be employed to prepare reference materials for peptide synthesis analytics, supporting quality-by-design approaches in fine chemical synthesis and peptide intermediate characterization.
6. Pharmaceutical Intermediate Preparation
N-α-Boc-N-im-dinitrophenyl-L-histidine is relevant to pharmaceutical intermediate preparation where histidine-containing building blocks must be manufactured with controlled protection and stereochemical integrity. The protected α-amino group enables scalable peptide coupling chemistry, while the N-im dinitrophenyl imidazole protection helps manage side-chain reactivity during intermediate handling and downstream transformations. The orthogonal protection pattern supports stepwise deprotection to yield functional histidine residues for incorporation into active pharmaceutical ingredient (API) precursors, peptide-like intermediates, or synthesis of drug-candidate scaffolds. The compound's defined structure makes it suitable for process chemistry intermediate preparation and specialty chemical production routes that require reproducible amino acid derivative quality attributes.
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