N-α,N-ε-di-Z-L-lysine is a protected lysine derivative bearing two benzyloxycarbonyl (Z, Cbz) protecting groups on the α-amino and ε-amino functionalities, with the remaining carboxyl group present as the free acid and the side chain retaining the characteristic (CH2)4 chain of lysine. The molecule contains both an α-carboxyl group and a protected α-amino group, while the ε-amino group is also carbamate-protected, and the "L" designation indicates the stereochemical configuration at the α-carbon. As a bis-carbamate-protected amino acid, it is employed as a stepwise building block in peptide synthesis where orthogonal control of amine reactivity is required, and the protected amines help suppress undesired side reactions during coupling and deprotection sequences.
CAT No: CP01463
CAS No:405-39-0
Synonyms/Alias:Z-Lys(Z)-OH;405-39-0;(S)-2,6-Bis(((benzyloxy)carbonyl)amino)hexanoicacid;N,N'-Dibenzyloxycarbonyl-L-lysine;SBB058133;N,N'-Bis(benzyloxycarbonyl)-L-lysine;N,N'-Di-Cbz-L-lysine;N2,N6-Bis[(phenylmethoxy)carbonyl]-L-lysine;L-Lysine,N2,N6-bis[(phenylmethoxy)carbonyl]-;(2S)-2,6-bis(phenylmethoxycarbonylamino)hexanoicacid;Nalpha,Nepsilon-Di-Z-L-lysine;(2S)-2,6-bis[(phenylmethoxy)carbonylamino]hexanoicacid;Cbz-Lys(Z)-OH;AC1OJJ91;N|A,N|A-Di-Z-L-lysine;KSC583G0T;96835_ALDRICH;SCHEMBL464715;N2,N6-Dicarbobenzoxy-L-lysine;96835_FLUKA;CTK4I3309;BLZXFNUZFTZCFD-IBGZPJMESA-N;MolPort-001-793-041;ZINC4521940;ANW-43412
N-α,N-ε-di-Z-L-lysine is a protected L-lysine derivative bearing two benzyloxycarbonyl (Z, Cbz) groups at both the α-amino and ε-amino positions, yielding a diamine-protected amino acid with a stereogenic center at the α-carbon. The molecule retains the carboxylic acid functionality while masking both primary amines as carbamate-protected groups, which strongly modulates nucleophilicity and prevents undesired side reactions during peptide coupling. The Z carbamates are typically stable under many peptide synthesis conditions yet can be removed selectively by hydrogenolysis, enabling staged deprotection for orthogonal functionalization strategies. The resulting chiral, bis-protected lysine building block is well suited for constructing well-defined peptide sequences and for preparing downstream lysine-derived intermediates with controlled chemoselectivity.
1. Peptide Synthesis
N-α,N-ε-di-Z-L-lysine is applied in peptide synthesis workflows where lysine residues require orthogonal control of both the α- and side-chain amines. The α-carboxylic acid and the α-Z-protected amino group support standard amino-acid coupling chemistry, while the ε-Z carbamate protects the side-chain during chain assembly to minimize branching and cross-linking. Hydrogenolysis-based deprotection can be used to unmask the ε-amine after peptide elongation, enabling subsequent acylation, guanidylation, or further peptide fragment coupling. The bis-protected lysine structure therefore functions as a chiral, peptide-compatible intermediate for generating lysine-containing peptides and peptide analogs with defined side-chain substitution patterns.
2. Side-Chain Functionalization
N-α,N-ε-di-Z-L-lysine serves in side-chain functionalization programs that require controlled access to the lysine ε-amine after selective deprotection. The ε-Z carbamate masks the primary amine during initial synthetic steps, supporting sequential derivatization without premature reaction of the side chain. After removing the appropriate Z group(s), the liberated ε-amine can participate in forming amide linkages, urea/thiourea motifs, or other nitrogen-containing functionalities used to tune binding properties and molecular recognition. The protected lysine framework thus supports targeted amino acid derivatization and downstream synthesis of functionalized lysine-containing scaffolds used in chemical biology and materials-facing conjugation chemistry.
3. Bioconjugation Chemistry
N-α,N-ε-di-Z-L-lysine is suitable for bioconjugation chemistry where lysine-reactive handles must be introduced with controlled chemoselectivity. The presence of two Z-protected amines reduces nonspecific reactivity during intermediate preparation, allowing the compound to be carried through peptide or linker assembly steps before generating an amine-bearing conjugation site. Selective deprotection of the ε-amino carbamate can provide a defined nucleophile for coupling to activated esters, isothiocyanates, aldehydes, or other electrophiles commonly used to create stable amide or urea linkages. The chiral lysine backbone and protected-group strategy make the compound compatible with constructing conjugation-ready peptide fragments and linker modules for biomolecule labeling workflows.
4. Process Chemistry Intermediate
N-α,N-ε-di-Z-L-lysine is used as a manufacturing-oriented intermediate for producing protected lysine building blocks and peptide-grade components with predictable reactivity profiles. The bis-carbamate protection pattern suppresses amine-mediated side reactions during isolation, purification, and subsequent coupling steps, which can simplify downstream handling in fine chemical synthesis. The carboxylic acid functionality supports conversion into coupling-ready derivatives under controlled process conditions, while the Z groups provide a robust protection strategy that can be removed on demand to reveal lysine functionality. The compound's defined stereochemistry and stable protecting-group chemistry make it applicable to scalable routes for protected amino acid supply chains supporting peptide manufacturing and industrial chemical production programs.
5. Peptidomimetics And SAR Studies
N-α,N-ε-di-Z-L-lysine is applied in peptidomimetic construction and structure-activity relationship studies requiring lysine side-chain incorporation with controlled substitution. The protected ε-amine allows installation of side-chain modifications that can mimic post-translationally derived lysine states or introduce non-native functional groups while preserving the peptide backbone stereochemical integrity. Sequential deprotection and derivatization enable generation of libraries of lysine-modified analogs, including amide- or urea-containing variants that influence charge distribution and hydrogen-bonding networks. The compound therefore supports SAR-driven exploration of lysine-dependent binding motifs through chemically defined peptide analog synthesis and systematic amino acid modification strategies.
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