N-α-Fmoc-N-ε-2-chloro-Z-L-lysine is a protected lysine derivative in which the α-amino group is Fmoc-protected and the ε-amino group is Z-protected, with a 2-chloro substituent on the ε-amino protecting group. The molecule contains both a carboxyl functional group and protected amino functionalities, and the presence of the Fmoc and Z groups suppresses undesired amine reactivity during peptide-coupling steps while the L-lysine backbone provides the characteristic lysine side-chain geometry. In peptide synthesis and related chemical biology workflows, it functions as a stepwise building block for introducing a lysine residue bearing a chlorinated side-chain handle or for preparing chlorinated lysine-containing peptide and amino acid conjugates under controlled chemoselectivity.
CAT No: CP01439
CAS No:133970-31-7
Synonyms/Alias:Fmoc-Lys(2-Cl-Z)-OH;133970-31-7;Fmoc-Lys(2-Cl-Cbz)-OH;n-(9-fluorenylmethyloxycarbonyl)-n'-(2-chlorobenzyloxycarbonyl)-l-lysine;C29H29ClN2O6;MolPort-003-983-046;CF-189;FC1244;AKOS015895286;AKOS015924142;ZINC100018490;AK-81203;ST24047284;ST51052860
N-α-Fmoc-N-ε-2-chloro-Z-L-lysine is a protected L-lysine derivative designed for orthogonally protected peptide chemistry, featuring an Fmoc group on the α-amino function and a Z (benzyloxycarbonyl) protecting group on the ε-amino side chain. The molecule also contains a stereogenic α-carbon consistent with L-lysine configuration and a side-chain bearing a reactive 2-chloro substituent that can participate in nucleophilic substitution or serve as a handle for subsequent functionalization. The presence of two carbamate-protected amines suppresses undesired coupling and enables controlled deprotection sequences during solid-phase or solution-phase peptide assembly. The chlorinated side-chain and protected amine pattern make the compound a chiral, functionalized amino acid building block and a downstream intermediate for amino acid derivatization, peptidomimetic design, and side-chain modification strategies.
1. Peptide Synthesis
N-α-Fmoc-N-ε-2-chloro-Z-L-lysine is applied in peptide synthesis workflows where orthogonal N-protection supports sequential coupling and selective deprotection. The Fmoc-protected α-amino group is compatible with standard peptide coupling chemistry after base-mediated Fmoc removal, while the Z-protected ε-amino group remains masked to prevent cross-reactivity during chain elongation. The lysine backbone geometry and L-stereochemistry support incorporation into peptide sequences with defined side-chain placement, and the 2-chloro handle can be retained for later side-chain diversification. The resulting peptide building block enables construction of protected lysine-containing intermediates that can be converted into chlorinated lysine analogs and subsequently used for peptide analog generation and structure-focused studies.
2. Side-Chain Functionalization
N-α-Fmoc-N-ε-2-chloro-Z-L-lysine is utilized for side-chain functionalization strategies that convert a chlorinated lysine motif into more reactive or conjugation-ready functionalities. The ε-amine is protected as a Z carbamate, allowing the 2-chloro substituent on the side chain to function as a synthetic handle for nucleophilic substitution, substitution-driven diversification, or incorporation into electrophile-based derivatization schemes. The preserved stereocenter and the protected amine pattern help maintain chemoselectivity during transformations that target the chlorinated site rather than the backbone. Downstream derivatives can be used to generate amino acid-modified scaffolds, peptidomimetic fragments, or functionalized peptide side chains that support chemical biology experiments and materials-oriented conjugation chemistry.
3. Chemical Biology Labeling
N-α-Fmoc-N-ε-2-chloro-Z-L-lysine is applied in chemical biology research for preparing lysine-containing probes and reactive peptide fragments used in labeling and biomolecule modification. The orthogonally protected amines enable controlled assembly of peptide sequences or peptide-like constructs, while the 2-chloro functionality can be used as a reactive site for subsequent conjugation to nucleophiles present in target biomolecules or affinity tags. The Fmoc and Z carbamates provide a protected intermediate stage that can be carried through synthesis without premature side reactions, supporting reproducible probe preparation. The chlorinated side-chain thus serves as a tunable electrophilic motif that can be introduced into peptide-based reagents, enabling downstream generation of labeled constructs for molecular recognition studies and biochemical assay development.
4. Peptidomimetics And SAR Studies
N-α-Fmoc-N-ε-2-chloro-Z-L-lysine is suitable for peptidomimetic construction and structure-activity relationship (SAR) studies where lysine side-chain chemistry is systematically varied. The compound's L-lysine stereochemistry and dual N-protection allow incorporation into analog libraries while maintaining consistent backbone orientation and side-chain positioning across series. The 2-chloro substituent enables controlled diversification into alternative side-chain functionalities, supporting SAR workflows that correlate chemical modifications with binding or recognition properties in vitro. The protected amino acid derivative format also supports parallel synthesis of analogs as defined intermediates, facilitating comparative evaluation of structure-defined peptide mimetics and related molecular scaffolds.
5. Pharmaceutical Intermediate Preparation
N-α-Fmoc-N-ε-2-chloro-Z-L-lysine is employed as a chiral, protected amino acid intermediate in pharmaceutical manufacturing-adjacent fine chemical synthesis where functionalized lysine motifs are required for downstream active ingredient or intermediate construction. The Fmoc carbamate and Z carbamate protections provide stability during multi-step processing and allow predictable deprotection sequences aligned with peptide-coupling or fragment assembly operations. The chlorinated side-chain can be carried into later synthetic stages to generate substituted lysine derivatives that serve as intermediates for larger, more complex molecules. The compound's defined stereochemistry and protected functional group arrangement support reproducible intermediate preparation for process chemistry routes that rely on amino acid-derived chiral building blocks.
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