N-α,e-di-Boc-L-lysine dicyclohexylamine salt is a protected lysine derivative in which the α-amino group and the ε-amino side chain are each masked as Boc carbamates, and the molecule bears the free carboxyl group characteristic of an amino acid scaffold. The stereochemistry is specified as L for the α-carbon, and the counterion dicyclohexylamine forms a salt with the carboxylate, while the Boc groups provide chemoselective stability toward many side reactions during peptide-coupling sequences. In synthesis, this protected, salt-form amino acid is used as a stepwise building block for preparing lysine-containing peptides and peptide fragments, where controlled deprotection of Boc groups enables sequential access to the α- and ε-amino functionalities for further bond formation.
CAT No: CP01416
N-α,e-di-Boc-L-lysine dicyclohexylamine salt is a protected lysine derivative in which the α-amino group and the ε-amino side chain are both carbamated with Boc groups, preserving the L-lysine stereocenter while masking primary amine nucleophilicity. The dicyclohexylamine salt form improves handling of the bis-Boc amino acid by pairing the zwitterionic/acidic sites with a bulky, non-nucleophilic counterion, which can influence crystallinity and filtration behavior during peptide building block preparation. The molecule therefore presents two orthogonally "latent" amine functionalities that can be revealed through controlled Boc deprotection, enabling stepwise peptide coupling and side-chain functionalization. The protected lysine framework also provides a stable, transportable chiral intermediate for downstream synthesis of amide-linked peptides, protected amino acid derivatives, and lysine-based scaffolds in both research and industrial fine chemical workflows.
1. Peptide Synthesis
N-α,e-di-Boc-L-lysine dicyclohexylamine salt functions as a lysine peptide building block for solid-phase or solution-phase peptide synthesis where both the α- and ε-amines must be protected during chain assembly. The bis-Boc protection pattern suppresses undesired side reactions from the two primary amines, while the L-configuration maintains stereochemical integrity at the lysine α-carbon during coupling chemistry. Controlled Boc removal strategies can later generate a free ε-amine for selective branching, crosslinking, or post-synthetic modification after the peptide backbone is formed. The resulting lysine-containing peptides and peptide fragments can be used to construct defined sequences for biochemical research, peptide standards, and peptidomimetic libraries that require precise amine positioning.
2. Side-Chain Functionalization
N-α,e-di-Boc-L-lysine dicyclohexylamine salt supports side-chain functionalization workflows in chemical biology and synthetic organic chemistry by providing a protected ε-amine handle that can be unveiled on demand. The ε-Boc group enables sequential deprotection and subsequent derivatization into amide, urea, sulfonamide, or other nitrogen-containing linkages while minimizing cross-reactivity during earlier steps. The presence of both α- and ε-protecting carbamates allows preparation of lysine intermediates that can be conjugated to electrophiles or activated carboxylic acids with controlled chemoselectivity. Downstream products include functionalized lysine analogs for affinity probes, linker components for conjugates, and intermediates used to generate structured scaffolds for SAR studies and molecular recognition investigations.
3. Protected Amino Acid Chemistry
N-α,e-di-Boc-L-lysine dicyclohexylamine salt is suitable for protected amino acid synthesis routes that require a stable, chiral, bis-amine-blocked lysine intermediate. The dual Boc groups provide predictable acid-labile protection behavior, supporting orthogonal deprotection planning when paired with other protecting-group sets in multi-amino-acid syntheses. The salt form can be leveraged to improve processability during intermediate preparation, including weighing, dissolution, and isolation steps commonly encountered in peptide building block manufacturing. The compound can be converted into alternative protected lysine derivatives, activated forms for coupling, or protected side-chain reagents used to build amine-rich motifs in fine chemical synthesis and applied peptide science.
4. Bioconjugation Chemistry
N-α,e-di-Boc-L-lysine dicyclohexylamine salt serves as a precursor for bioconjugation chemistry where lysine side-chain amines are required for controlled attachment to biomolecular targets. The protected ε-amine can be liberated under conditions compatible with the peptide or linker context, enabling formation of stable conjugation linkages such as amide bonds to activated esters or carbodiimide-derived intermediates. The bis-Boc architecture helps maintain low background reactivity during linker synthesis and intermediate storage, supporting stepwise assembly of conjugation-ready components. Resulting conjugates and lysine-functionalized linkers can be applied in chemical biology research, biomolecule labeling strategies, and analytical reagent preparation where defined amine density and chemoselectivity matter.
5. Pharmaceutical Manufacturing
N-α,e-di-Boc-L-lysine dicyclohexylamine salt can be employed in pharmaceutical manufacturing supply chains as a process-relevant, chiral lysine intermediate for producing protected peptide segments and amine-functional excipients. The α- and ε-amines are masked as Boc carbamates, which supports controlled coupling chemistry and reduces impurity formation from free amine reactivity during upstream synthesis. The dicyclohexylamine salt form may aid reproducible handling and isolation in industrial fine chemical production, aligning with manufacturing needs for consistent intermediate quality and downstream conversion. The compound's structure enables integration into scalable peptide and peptidomimetic manufacturing workflows where lysine-containing sequences and defined side-chain functionalities are required for subsequent processing steps.
6. Process Chemistry Intermediates
N-α,e-di-Boc-L-lysine dicyclohexylamine salt is applicable to process chemistry intermediate preparation for routes that demand a chiral, bis-protected amino acid with predictable deprotection logic. The protected lysine backbone supports conversion into activated coupling partners or further protected derivatives while maintaining stereochemical fidelity and minimizing side reactions from the two amine sites. The salt counterion and bis-Boc protection can be used to tune physical properties relevant to filtration, crystallization, and handling in multi-step synthesis planning. The compound thereby serves as a practical intermediate for specialty chemical production, including the manufacture of protected amino acid building blocks, peptide coupling reagents, and lysine-based fragments used across industrial peptide science and synthetic methodology development.
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