Fmoc-L-His(Boc)-OH*DCHA contains the amino acid histidine in a protected, stepwise peptide-synthesis-ready form, bearing an Fmoc group on the α-amino functionality and a Boc-protected side-chain on the imidazole-bearing histidine moiety. The molecule includes a free carboxylic acid (-COOH) and an imidazole nitrogen protected as a tert-butoxycarbonyl carbamate, with the "L" designation indicating the stereochemical configuration at the α-carbon while the "*DCHA" denotes a dicyclohexylamine counterion associated with the carboxylate/overall salt form. In synthesis and materials research, it is employed as a protected amino acid building block for controlled coupling chemistry and for preparing histidine-containing peptide derivatives, while the salt form can support handling and dissolution behavior in peptide workflows and related analytical sample preparation.
CAT No: CP25603
CAS No:210820-99-8
Synonyms/Alias:210820-99-8;Fmoc-L-His(Boc)-OHDCHA;Fmoc-His(Boc)-OHcyclohexylammoniumsalt;Fmoc-His(Boc)-OHCHA;C26H27N3O6.C6H13N;PubChem12426;Fmoc-His(Boc)-OHCHA;47515_FLUKA;MolPort-003-934-138;CF-184;AKOS016014022;Fmoc-His(Boc)-OHcyclohexylaminesalt;AK130130;KB-300444;V1357;K-6073;Nim-Boc-N|A-Fmoc-L-histidinecyclohexylammoniumsalt;N|A-Fmoc-N(im)-Boc-L-histidinecyclohexylammoniumsalt;Nim-Boc-Nalpha-Fmoc-L-histidinecyclohexylammoniumsalt;Nalpha-Fmoc-N(im)-Boc-L-histidinecyclohexylammoniumsalt;N-alpha-(9-Fluorenylmethyloxycarbonyl)-n-im-(t-butyloxycarbonyl)-L-histidinecyclohexylamine;N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-1-{[(2-methyl-2-propanyl)oxy]carbonyl}-L-histidinecyclohexanamine
Chemical Name:N-alpha-(9-Fluorenylmethyloxycarbonyl)-N-im-(t-butyloxycarbonyl)-L-histidine dicyclohexylamine
Fmoc-L-His(Boc)-OH·DCHA is an Fmoc-protected L-histidine derivative bearing a Boc-protected side-chain imidazole and supplied as a dicyclohexylamine (DCHA) salt. The molecule contains a chiral α-amino acid core with an Fmoc carbamate on the nitrogen, a free carboxylic acid for controlled coupling, and a Boc-protected imidazole that can be selectively unmasked under established deprotection conditions. The imidazole ring's basicity is masked by Boc, reducing side reactions during peptide assembly while enabling later conversion to histidine-like functionality. The salt form improves handling and solid-state properties for synthetic workflows that require reproducible amino acid building block dosing in peptide synthesis and downstream derivatization.
1. Peptide Synthesis
Fmoc-L-His(Boc)-OH·DCHA is used in solid-phase peptide synthesis where the Fmoc group supports orthogonal N-protection and the Boc-protected histidine side chain suppresses imidazole-mediated side reactions during coupling cycles. The free carboxylic acid participates in standard peptide coupling chemistry, while the protected imidazole maintains controlled chemoselectivity for multi-residue sequences. Unmasking strategies can later reveal the histidine side chain for metal-binding or pH-responsive behavior within peptide scaffolds. The resulting histidine-containing peptides can be generated for structure-activity relationship studies, protein fragment mapping, and peptide library construction.
2. Protein Engineering
Fmoc-L-His(Boc)-OH·DCHA serves as a chiral amino acid building block for incorporating histidine residues into engineered protein fragments and peptide mimics used in protein engineering workflows. The Fmoc-protected α-amino group enables stepwise assembly, whereas the Boc-protected imidazole minimizes undesired nucleophilicity and side-chain crosslinking during synthesis of histidine-rich constructs. Deprotection restores the imidazole functionality, enabling histidine-dependent coordination motifs and local protonation effects that influence binding interfaces. The compound therefore supports generation of sequence-defined variants used for mechanistic studies of protein recognition and engineered binding-site design.
3. Bioconjugation Chemistry
Fmoc-L-His(Boc)-OH·DCHA can be applied to bioconjugation and chemical biology workflows that require controlled introduction of histidine-containing linkers or capture handles onto biomolecules. The protected imidazole reduces off-target reactivity during linker synthesis, while the carboxylic acid and Fmoc-protected amine can be transformed into conjugation-ready intermediates through orthogonal deprotection and functional group conversion. Restored histidine side chains can participate in metal-affinity strategies or pH-dependent interactions when incorporated into peptide tags and conjugates. Downstream products include histidine-bearing peptide conjugates for analytical binding assays, biomolecule labeling, and scaffolded molecular probes.
4. Peptidomimetics And SAR
Fmoc-L-His(Boc)-OH·DCHA is suitable for peptidomimetic construction and SAR studies where histidine's imidazole contributes to hydrogen bonding, metal coordination, and protonation-state modulation. The dual protection pattern, Fmoc on the α-amino group and Boc on the imidazole, helps maintain chemoselectivity during scaffold assembly and allows later side-chain activation to tune interaction properties. The protected amino acid nature supports incorporation into constrained analogs, including cyclic or side-chain-modified peptide mimics, by enabling controlled deprotection and subsequent derivatization. The resulting histidine-containing analogs can be used to probe structure-function relationships in receptor-binding and enzyme-recognition contexts.
5. Pharmaceutical Intermediate Preparation
Fmoc-L-His(Boc)-OH·DCHA is employed in pharmaceutical intermediate preparation for manufacturing routes that require protected amino acid derivatives compatible with peptide-coupling steps and controlled deprotection sequences. The Fmoc carbamate and Boc-protected imidazole provide a stable protection scheme that can be carried through intermediate isolation and subsequent conversion into defined amide or peptide linkages. The salt form supports reproducible solids handling and can facilitate consistent feeding in fine chemical synthesis where batch-to-batch dosing matters. Downstream utility includes preparation of histidine-containing fragments used in manufacturing of peptide-like intermediates, process-scale building blocks, and defined chemical entities requiring orthogonally protected functionality.
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