Boc-Dab(Alloc)-OH (dicyclohexylammonium) salt is a protected amino acid derivative featuring a Dab (2,4-diaminobutyric acid) backbone bearing an N-Boc group and an Alloc (allyloxycarbonyl) protecting group on the side-chain amino functionality. The molecule contains a free carboxylic acid (-COOH) while its basic amines are protected or present as the dicyclohexylammonium counterion, and the Boc and Alloc groups modulate chemoselectivity by reducing undesired nucleophilic reactions during peptide-coupling steps. This salt-form, protected intermediate is used in amino acid and peptide synthesis workflows to enable stepwise functionalization and controlled deprotection of orthogonally protected amines for preparing more complex amino acid and peptide derivatives.
CAT No: CP05308
CAS No:327156-92-3
Synonyms/Alias:N-α-Boc-N-γ-allyloxycarbonyl-L-2,4-diaminobutyricaciddicyclohexylaminesalt;327156-92-3;Dicyclohexylamine(S)-4-(((allyloxy)carbonyl)amino)-2-((tert-butoxycarbonyl)amino)butanoate;Boc-Dab(Alloc)-OH(dicyclohexylammonium)salt;81717_ALDRICH;81717_FLUKA;CTK8C0041;MolPort-003-939-162;ANW-63927;AKOS016003816;AK-61257;Boc-Dab(Alloc)-OHdicyclohexylaminesalt;Boc-Dab(Alloc)-OHdicyclohexylammoniumsalt;RT-021675;ST24046507;N|A-Alloc-N|A-Boc-L-2,4-diaminobutyricacid(dicyclohexylammonium)salt;N|A-Boc-N|A-Alloc-L-2,4-diaminobutyricacid(dicyclohexylammonium)salt;Nalpha-Boc-Ngamma-Alloc-L-2,4-diaminobutyricaciddicyclohexylaminesalt;Ngamma-Alloc-Nalpha-Boc-L-2,4-diaminobutyricaciddicyclohexylaminesalt;Nalpha-Boc-Ngamma-Alloc-L-2,4-diaminobutyricacid(dicyclohexylammonium)salt;Ngamma-Alloc-Nalpha-Boc-L-2,4-diaminobutyricacid(dicyclohexylammonium)salt
Boc-Dab(Alloc)-OH (dicyclohexylammonium) salt is a protected lysine-like amino acid building block featuring a Boc-protected α-amino group and an Alloc-protected side-chain amine on a chiral Dab (2,4-diaminobutyric acid) backbone, supplied as a dicyclohexylammonium salt. The molecule contains a free carboxylic acid for peptide coupling, while the orthogonal protecting groups enable sequential deprotection and controlled functionalization of both the α- and side-chain nitrogen atoms. The Alloc group can be removed under palladium-mediated conditions, whereas the Boc group is acid-labile, supporting orthogonal protection strategies commonly used in protected amino acid synthesis. Salt formation with dicyclohexylamine can improve handling and crystallinity for downstream peptide building block preparation, while the dual protected amines provide predictable reactivity for amide bond formation and side-chain derivatization.
1. Peptide Synthesis
Boc-Dab(Alloc)-OH (dicyclohexylammonium) salt is used in peptide synthesis workflows where orthogonally protected diamino acid residues are required for stepwise chain assembly. The Boc-protected α-amino group supports conventional peptide coupling at the carboxylic acid terminus, while the Alloc-protected side-chain amine remains masked during iterative elongation. Alloc deprotection enables selective side-chain functionalization after the peptide backbone is assembled, supporting intramolecular cyclization, branching, or attachment of solubilizing and recognition motifs. The resulting peptide analogs can be prepared for structure-activity relationship studies and chemical biology probes that require controlled presentation of a side-chain amine at defined positions.
2. Side-Chain Functionalization
Boc-Dab(Alloc)-OH (dicyclohexylammonium) salt is applied to side-chain functionalization strategies in synthetic organic chemistry targeting amino group diversification. The Alloc-protected amine on the Dab side chain can be unveiled while the Boc group remains intact, allowing selective formation of urea, sulfonamide, carbamate, or amide derivatives through targeted acylation or sulfonylation chemistry. The presence of a carboxylic acid and Boc protection supports downstream conversion into activated peptide coupling partners or further protected intermediates without premature side-chain reaction. Side-chain modified Dab-containing derivatives can serve as intermediates for peptidomimetics, molecular scaffolds, and amine-tagged constructs used in biochemical assays and materials-oriented conjugation chemistry.
3. Chemical Biology Probes
Boc-Dab(Alloc)-OH (dicyclohexylammonium) salt is suitable for chemical biology and biomolecule modification efforts that require defined, orthogonally addressable amines within peptide or peptide-like frameworks. The dual-protected amine architecture enables controlled installation of labels or affinity handles by first assembling the peptide using the carboxyl group and Boc-protected α-amine, then selectively removing Alloc to expose the side-chain amine for conjugation. The resulting functionalized peptides can be employed to generate probes for receptor binding studies, protein interaction mapping, or enzyme-substrate analog design where amine positioning influences molecular recognition. The compound's protected amino acid form supports reproducible synthesis of labeled intermediates that can be further processed into conjugates for analytical research and targeted molecular tools.
4. Peptidomimetics And SAR
Boc-Dab(Alloc)-OH (dicyclohexylammonium) salt is utilized in peptidomimetic construction and SAR studies where incorporation of a diamino acid residue improves scaffold control and side-chain charge distribution. The Dab backbone provides a stereodefined chiral center and a side-chain amine that can be selectively unmasked and derivatized to tune hydrogen-bonding patterns and electrostatic properties. Boc and Alloc protecting-group orthogonality supports iterative scaffold elaboration, including formation of cyclic constraints, attachment of pharmacophore fragments, or introduction of solubilizing substituents. Peptidomimetic libraries derived from this building block can be generated for structure-activity relationship investigations and fragment-based molecular design campaigns, enabling systematic evaluation of how side-chain chemistry impacts binding-relevant conformations.
5. Pharmaceutical Intermediate Preparation
Boc-Dab(Alloc)-OH (dicyclohexylammonium) salt is relevant to pharmaceutical intermediate preparation where protected amino acid derivatives are required for controlled synthesis of amine-functionalized peptide segments. The carboxylic acid functionality enables formation of activated intermediates for peptide coupling, while Boc and Alloc groups provide a practical route to orthogonally manage α- and side-chain nitrogens during multi-step manufacturing. Alloc deprotection compatibility supports downstream installation of functional groups used to adjust solubility, stability, or linker chemistry in peptide-based intermediates. The dicyclohexylammonium salt form can support consistent handling in fine chemical production, facilitating scalable protected building block workflows for peptide analog manufacturing and process chemistry intermediate generation.
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