N-α-Allyloxycarbonyl-N-ε-Boc-Dlysine dicyclohexylamine salt is a protected, amino acid derivative of lysine bearing an Nα allyloxycarbonyl (Alloc) group and an Nε tert-butoxycarbonyl (Boc) group, with the D stereochemical form indicated by the product name. The molecule contains both α-amino and α-carboxyl functionality masked as a protected amino acid framework, while the side-chain ε-amino group is protected as Boc, and the carboxylate is paired with dicyclohexylamine to form the corresponding salt. In peptide and amino acid synthesis workflows, the orthogonal combination of Alloc and Boc protecting groups supports stepwise chemoselective deprotection and coupling strategies for incorporating D-lysine derivatives into protected peptide intermediates, as well as for preparing labeled or structurally defined lysine-containing constructs.
CAT No: CP01410
N-α-Allyloxycarbonyl-N-ε-Boc-Dlysine dicyclohexylamine salt is a protected D-lysine derivative in which the α-amino group is masked as an allyloxycarbonyl (Alloc) carbamate and the ε-amino side chain is protected as a Boc carbamate. The zwitterionic lysine framework is present as a dicyclohexylamine salt, improving handling of the amino acid building block while maintaining the protected functional groups required for stepwise synthesis. The molecule contains a stereogenic center at the lysine α-carbon (D-configuration), and its orthogonally protected amines enable controlled sequential deprotection and selective peptide coupling. The Alloc and Boc groups define a predictable reactivity profile: the allyl carbamate can be removed under orthogonal conditions, while the Boc group can be removed under acid-mediated strategies, supporting robust downstream conversion to peptide fragments and functionalized lysine derivatives.
1. Peptide Synthesis
N-α-Allyloxycarbonyl-N-ε-Boc-Dlysine dicyclohexylamine salt supports peptide building block preparation for solid-phase or solution-phase synthesis where orthogonal amine protection is required. The protected α-amine (Alloc) and protected ε-amine (Boc) allow selective N-terminal incorporation and controlled side-chain functionalization, aligning with lysine-containing peptide assembly and late-stage derivatization workflows. Alloc deprotection can generate a free lysine α-amino or ε-amino handle depending on the synthetic stage, while Boc stability during coupling steps helps maintain sequence fidelity. The resulting lysine residue can be carried into peptide analog construction, enabling generation of mono- or di-functional lysine motifs for biochemical research and peptide science.
2. Chemical Biology
N-α-Allyloxycarbonyl-N-ε-Boc-Dlysine dicyclohexylamine salt is suitable for chemical biology applications that require controlled lysine reactivity for probe installation and biomolecule modification. The orthogonally protected amines provide a programmable route to expose a single nucleophilic site for conjugation while keeping the other amine masked to reduce side reactions. The D-stereochemistry can be leveraged when stereodefined lysine analogs are needed for structure-function studies, receptor-binding assays, or enzyme recognition experiments using non-native stereochemical patterns. Downstream deprotection and derivatization can yield lysine-containing linkers, affinity handles, or labeled peptide fragments that integrate into target-specific chemical biology toolkits.
3. Protected Amino Acids
N-α-Allyloxycarbonyl-N-ε-Boc-Dlysine dicyclohexylamine salt functions as an orthogonally protected lysine intermediate for protected amino acid synthesis and stepwise functional group management. The Alloc carbamate and Boc carbamate combination provides a separation of deprotection regimes, enabling sequential liberation of amine functionalities without cross-reactivity that would otherwise complicate multi-step peptide construction. The dicyclohexylamine salt form can improve practical handling of the amino acid derivative during synthesis and intermediate isolation, while the core lysine scaffold remains available for conversion into activated coupling partners. The compound can be employed to prepare N- and side-chain modified lysine derivatives, including C-terminal or side-chain derivatized intermediates used in fine chemical synthesis and peptide methodology development.
4. Side-Chain Functionalization
N-α-Allyloxycarbonyl-N-ε-Boc-Dlysine dicyclohexylamine salt enables side-chain functionalization strategies that exploit the lysine ε-amine as a controlled synthetic handle. The Boc-protected ε-amine can be maintained through peptide coupling steps, then selectively removed to generate a nucleophilic ε-amino group suitable for acylation, alkylation, or attachment of electrophilic tags and linkers. The orthogonal Alloc protection on the α-amino group supports selective exposure patterns that help tune regioselectivity for mono-substituted versus bis-substituted lysine derivatives. The resulting functionalized lysine building blocks can be carried into peptidomimetics, affinity reagents, and scaffold elaboration programs where defined lysine substitution patterns drive downstream molecular recognition.
5. Pharmaceutical Manufacturing
N-α-Allyloxycarbonyl-N-ε-Boc-Dlysine dicyclohexylamine salt can be applied in pharmaceutical manufacturing workflows that require reproducible, stereochemically defined protected amino acid inputs for peptide or peptide-like intermediate production. The orthogonal Alloc/Boc protection strategy supports controlled deprotection sequences during intermediate elaboration, which can be integrated into process chemistry routes for manufacturing peptide fragments, protected lysine units, or late-stage functionalized intermediates. The presence of the dicyclohexylamine salt form aligns with industrial handling considerations for amino acid derivatives, supporting consistent dosing and material transfer during synthesis campaigns. The compound's protected lysine framework can therefore serve as a process-compatible intermediate for producing defined peptide building blocks used in industrial fine chemical production and applied peptide manufacturing.
6. Fine Chemical Synthesis
N-α-Allyloxycarbonyl-N-ε-Boc-Dlysine dicyclohexylamine salt is appropriate for fine chemical synthesis programs that require chiral amino acid derivatives bearing orthogonally protected amines. The D-lysine stereocenter and the two protected carbamates enable construction of tailored amide, urea, and carbamate linkages through downstream coupling chemistry after selective deprotection. The allyl carbamate and tert-butyl carbamate groups provide a chemically managed pathway for generating single or sequentially exposed nucleophiles, supporting synthesis of heteroatom-functionalized lysine analogs and peptidomimetic scaffolds. The compound can be employed as a chiral intermediate for producing research-grade amino acid derivatives, including specialized lysine-containing fragments used in SAR studies, combinatorial library synthesis, and analytical reference material preparation.
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