Boc-L-MeLys(Z)-OH*DCHA is a protected, amino-acid derivative of L-methylated lysine bearing an Nα-Boc (tert-butoxycarbonyl) protecting group and a Z-protected side-chain functionality, supplied as a dicyclohexylamine (DCHA) salt. The molecule contains both an amino and a carboxyl functional group, with the Boc group masking the α-amino reactivity and the Z substituent on the side chain providing chemoselective control during stepwise assembly of peptide frameworks while the DCHA counterion supports salt formation and handling. In synthesis and chemical biology workflows, this protected amino acid is used as a building block for preparing lysine-containing peptides or peptide-like conjugates, including targets that require controlled introduction of the methylated lysine side-chain motif and compatible protection patterns.
CAT No: CP25559
CAS No:201002-18-8
Synonyms/Alias:Boc-N-Me-Lys(Z)-OH.DCHA;201002-18-8
Chemical Name:N-alpha-t-Butyloxycarbonyl-N-alpha-methyl-N-epsilon-benzyloxycarbonyl-L-lysine dicyclohexylamine
Boc-L-MeLys(Z)-OH*DCHA is a Boc-protected lysine derivative bearing a side-chain Z-protected functionality, supplied as a dicyclohexylamine (DCHA) salt to improve handling and solid-state properties. The L-configuration and the orthogonally protected side chain make it a practical building block for assembling lysine-containing peptide segments where controlled side-chain reactivity is required. In peptide synthesis workflows, this protected lysine form is typically selected to maintain compatibility with Boc-based N-terminal chemistry while preserving the side-chain protecting group through coupling and deprotection steps.
1. Boc-Based Peptide Synthesis
Boc-L-MeLys(Z)-OH*DCHA is used as a lysine building block in Boc-based solid-phase peptide synthesis and solution-phase peptide assembly, particularly when a protected lysine side chain must survive the peptide elongation sequence. Researchers in custom peptide synthesis and peptide library production rely on the Boc amino protection to manage N-terminal chemistry, while the Z-protected side-chain functionality helps control downstream modifications after the peptide backbone is assembled. The DCHA salt form supports consistent weighing and improved formulation behavior for automated or semi-automated peptide workflows, helping teams maintain reproducible coupling inputs across multiple synthesis runs.
2. Lysine Side-Chain Functionalization
Boc-L-MeLys(Z)-OH*DCHA is commonly selected for projects that require lysine-derived side-chain chemistry at a later stage, such as preparing peptide intermediates for further derivatization. In chemical biology and protein engineering studies, the Z-protected lysine side chain provides a protected handle during initial peptide construction, allowing researchers to postpone side-chain unveiling until they reach the desired intermediate. This strategy is especially valuable when the peptide sequence contains multiple reactive functionalities that must be orthogonally managed to avoid cross-reactivity during coupling, purification, or post-assembly processing.
3. Protected Amino Acid Intermediate Development
Boc-L-MeLys(Z)-OH*DCHA serves as a downstream-ready protected amino acid intermediate for manufacturing peptide segments used in larger-scale synthesis of peptide-based research reagents. Pharmaceutical intermediate development groups and specialty chemical manufacturers use this type of protected lysine derivative to standardize building blocks for repeatable segment assembly, reducing variability between batches and enabling controlled deprotection schedules during final coupling steps. The combination of Boc protection, L-stereochemistry, and side-chain Z protection aligns with established industrial peptide chemistry practices where protecting-group compatibility and predictable intermediate handling are central to process reliability.
4. Peptide Segment Building Blocks
Boc-L-MeLys(Z)-OH*DCHA is applied in the preparation of lysine-containing peptide segments used in modular synthesis approaches, including fragment condensation and complex peptide assembly. Peptide chemists working on longer sequences or structured peptides often prefer a defined, protected lysine building block to ensure that the lysine position is introduced with the correct stereochemical configuration and side-chain protection state before fragment ligation. This supports smoother downstream purification and reduces the risk of premature side-chain reactions, which is particularly important when assembling peptides that will later undergo additional chemical transformations or conjugation steps.
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