Boc-Lys(Z)-OSu is a Boc-protected lysine derivative bearing a benzyloxycarbonyl (Z/Cbz) group on the side-chain and an N-hydroxysuccinimide (OSu) ester at the carboxyl terminus, placing it in the class of protected amino acid N-hydroxysuccinimide esters. The molecule contains a Boc carbamate that masks the alpha-amino functionality, while the OSu ester provides an activated carboxyl group for acyl transfer chemistry and the Z-protected lysine side chain retains a benzyloxycarbonyl-protected ε-amino functionality, with stereochemistry not specified in the name. Boc-Lys(Z)-OSu is used as a building block for stepwise peptide or amide bond formation where controlled chemoselectivity is required, and it can also serve as a reagent for preparing lysine-containing conjugates and labeled or modified peptide intermediates under conditions that react with N-hydroxysuccinimide-activated carboxyl groups.
CAT No: CP27034
CAS No:34404-36-9
Synonyms/Alias:Boc-Lys(Z)-OSu;34404-36-9;BOC-LYS(CBZ)-OSU;(S)-2,5-Dioxopyrrolidin-1-yl6-(((benzyloxy)carbonyl)amino)-2-((tert-butoxycarbonyl)amino)hexanoate;Nalpha-Boc-Nepsilon-Z-L-lysinehydroxysuccinimideester;Nepsilon-Z-Nalpha-Boc-L-lysinehydroxysuccinimideester;Nalpha-Boc-Nepsilon-Cbz-L-lysineN-hydroxysuccinimideester;15541_ALDRICH;SCHEMBL2803734;15541_FLUKA;MolPort-002-499-537;YWLICOCXPNQJPC-KRWDZBQOSA-N;CB-935;KM5661;SPB-30017;ZINC71788013;AKOS015923314;AKOS016002281;AK-43587;KB-91840;ST24035784;V1420;N|A-Boc-N|A-Z-L-lysinehydroxysuccinimideester;N|A-Z-N|A-Boc-L-lysinehydroxysuccinimideester;N|A-Boc-N|A-Cbz-L-lysineN-hydroxysuccinimideester
Boc-Lys(Z)-OSu is a protected lysine derivative designed for amide bond formation, combining a Boc-protected alpha-amino group with a side-chain Z-protected ε-amino functionality and an N-hydroxysuccinimide (OSu) ester at the carboxylate. This activated ester form makes it a practical coupling reagent building block for assembling lysine-containing peptide segments and for preparing lysine-functionalized intermediates where controlled protection of the reactive amines is required. Researchers in peptide synthesis and pharmaceutical intermediate development commonly select this type of lysine OSu ester to improve coupling efficiency while maintaining orthogonal protection of the side chain during downstream transformations.
1. Peptide Segment Coupling
Boc-Lys(Z)-OSu is used in peptide synthesis workflows to form amide linkages that incorporate lysine residues while keeping both the α-amino (Boc) and ε-amino (Z) functionalities protected. Peptide chemistry groups preparing lysine-containing fragments for custom peptide synthesis rely on the OSu activation to promote efficient coupling during segment condensation, particularly when assembling longer or more sterically demanding sequences. The protected side-chain amino group helps prevent undesired side reactions and supports consistent sequence integrity across multi-step assembly.
2. Protected Lysine Intermediate Synthesis
Boc-Lys(Z)-OSu serves as a lysine-based activated intermediate for building protected amide derivatives used in medicinal chemistry and peptide-derived intermediate libraries. Process development teams and synthetic chemists use OSu-activated amino acid derivatives to rapidly access amide-linked products while preserving the Boc and Z protection pattern for later deprotection and functional diversification. This makes the reagent a common choice when lysine functionality must be carried through as a protected handle rather than being consumed by premature reactions.
3. Solid-Phase Peptide Library Building
Boc-Lys(Z)-OSu is frequently selected for constructing lysine-bearing peptide libraries in parallel synthesis formats, where controlled coupling chemistry is essential for reproducible library members. Peptide array and library synthesis groups use the protected lysine OSu ester to introduce a lysine residue at a defined position while maintaining orthogonal protection of the ε-amino side chain for subsequent steps in the synthesis sequence. The reagent format supports downstream handling of protected peptide intermediates that can be carried into cleavage, purification, and final deprotection workflows.
4. Amide Linkage for Bioconjugation Precursors
Boc-Lys(Z)-OSu is used to generate protected lysine amide precursors that can later be converted into lysine-functionalized conjugation building blocks. Chemical biology and bioconjugation teams often prefer OSu-activated amino acid esters when they need efficient amide formation under controlled conditions while retaining protected amine groups for stepwise transformation. By maintaining the Boc/Z protection pattern during intermediate preparation, the reagent supports downstream development of lysine-containing conjugates and peptide-based linkers used in labeling and immobilization strategies.
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