Boc-L-His(Boc)-OH*Benzene is a protected amino acid derivative based on L-histidine, incorporating two Boc (tert-butoxycarbonyl) protecting groups on the imidazole side chain and the α-amino functionality. The molecule contains a free carboxylic acid group alongside Boc-protected amine and Boc-protected imidazole nitrogens, and the stereochemistry is specified as L for the α-carbon while the compound is present as a benzene adduct. In peptide synthesis and related amino acid coupling workflows, this bis-Boc protected histidine analogue functions as a protected building block that controls chemoselectivity by masking the side-chain and α-amino reactivity during stepwise assembly and can serve as a precursor for generating histidine-containing peptide derivatives after deprotection.
CAT No: CP25596
CAS No:20866-46-0
Synonyms/Alias:Boc-His(Boc)-OH;20866-46-0;(S)-3-(1-(tert-Butoxycarbonyl)-1H-imidazol-4-yl)-2-((tert-butoxycarbonyl)amino)propanoicacid;N,N'-Di-tert-butoxycarbonyl-L-histidine;(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-[1-[(2-methylpropan-2-yl)oxycarbonyl]imidazol-4-yl]propanoicacid;C16H25N3O6;PubChem12026;AC1ODZ1Y;Boc-His(Boc)-OH.DCHA;SCHEMBL3008885;CTK3J1699;IXHPIPUIOSSAIS-NSHDSACASA-N;MolPort-002-507-582;ZINC2584387;ANW-58552;CB-896;AKOS015892674;AKOS015924152;N-ALPHA,NIM-DI-BOC-L-HISTIDINE;AJ-43432;AK-80245;SC-25913;N,1-bis(tert-butoxy-carbonyl)-L-histidine;TC-147297;FT-0081976
Chemical Name:N-alpha-t-Butyloxycarbonyl-N-im-t-Butyloxycarbonyl-L-histidine Benzene
Boc-L-His(Boc)-OH*Benzene is a protected histidine building block supplied as a benzene solvate, featuring the amino group protected with a Boc (tert-butoxycarbonyl) group and the side-chain imidazole protected with an additional Boc group. This dual protection pattern stabilizes both the α-amino functionality and the imidazole side chain during peptide coupling, making the material a practical intermediate for assembling histidine-containing sequences where side-chain reactivity must be suppressed until the desired deprotection step. The benzene solvate form is commonly encountered for Boc-protected amino acid derivatives used in peptide synthesis workflows and related intermediate development.
1. Histidine-Containing Peptide Synthesis
Boc-L-His(Boc)-OH*Benzene is used by peptide chemistry groups to prepare histidine-containing peptides where the imidazole must remain protected throughout chain assembly. The Boc protection on the imidazole minimizes side reactions and helps maintain sequence integrity during coupling and deprotection cycles, supporting reliable synthesis of peptides that include histidine at specific positions. This protected histidine derivative is typically selected for custom peptide synthesis and library production when orthogonal handling of the imidazole is required during iterative assembly and purification.
2. Protected Segment Building Block
Boc-L-His(Boc)-OH*Benzene serves as a key protected amino acid segment component for solution-phase or fragment condensation strategies that require controlled reactivity of the histidine side chain. By keeping both the α-amino group and the imidazole protected, the building block supports downstream segment coupling steps without premature imidazole participation, which is especially valuable when assembling longer constructs or when histidine is embedded in sensitive sequence contexts. Researchers developing multi-step peptide intermediates often rely on this type of dual-Boc histidine protection to streamline purification and reduce side-product formation during segment assembly.
3. Pharmaceutical Peptide Intermediate Development
Boc-L-His(Boc)-OH*Benzene is frequently incorporated into the preparation of protected peptide intermediates used in medicinal chemistry programs that explore peptide-based leads and peptidomimetic scaffolds. The dual Boc protection helps ensure that histidine-containing intermediates remain chemically manageable during iterative functionalization and coupling steps, including the synthesis of advanced intermediates that later undergo controlled global deprotection and conversion to the target peptide sequence. In this context, the benzene solvate form is treated as part of the practical supply format for protected amino acid derivatives used in development-scale synthesis planning.
4. Peptide Library and SAR Workflows
Boc-L-His(Boc)-OH*Benzene supports peptide library synthesis and structure-activity relationship (SAR) studies where histidine variants or histidine-positioned analogs are compared under standardized synthetic conditions. Dual protection of the imidazole improves reproducibility across parallel syntheses by reducing variability from side-chain reactivity, which is important when generating multiple analogs for downstream analytical characterization. Medicinal chemistry and chemical biology laboratories commonly select this protected histidine building block to produce histidine-containing members of a library with consistent handling through coupling, deprotection, and purification steps.
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