Boc-Lys(2-chloro-Z)-OSu is a protected lysine-derived amino acid N-hydroxysuccinimyl ester (OSu) bearing an Nε-(2-chloro-Z) substituent and an N-terminal Boc (tert-butoxycarbonyl) protecting group. The molecule contains an activated carboxylate as the OSu ester, while the side-chain ε-amino functionality is masked by a 2-chloro-Cbz-type (Z) carbamate, and the Boc group controls chemoselectivity by preventing unprotected amide formation during coupling steps. In peptide chemistry and bioconjugation workflows, this activated ester form is used to transfer the lysine residue under conditions that promote amide bond formation with nucleophiles such as amines, while the orthogonal protection pattern supports stepwise assembly and minimizes side reactions from free amino groups.
CAT No: CP27340
CAS No:66438-39-9
Synonyms/Alias:Boc-Lys(2-Chloro-Z)-Osu;66438-39-9;C23H30ClN3O8;6403AH;ZINC71788038
Boc-Lys(2-chloro-Z)-OSu is a Boc-protected lysine derivative bearing a side-chain 2-chloro-Z protecting group and an N-hydroxysuccinimide (OSu) ester at the carboxylate, combining peptide-synthesis-ready functionality with an activated ester for amide bond formation. This reagent is typically handled as a protected amino acid building block for preparing lysine-containing peptide segments or for generating amide-linked intermediates under coupling conditions that leverage the OSu leaving group. The presence of the orthogonally protected lysine side chain supports controlled downstream assembly and selective deprotection strategies during peptide synthesis workflows.
1. Lysine Segment Coupling
Boc-Lys(2-chloro-Z)-OSu is used as an activated lysine building block for peptide segment coupling workflows where rapid amide bond formation is required. Researchers performing custom peptide synthesis and peptide library construction rely on the OSu ester to promote efficient coupling to amine-bearing partners while maintaining the lysine side chain in a protected state via the 2-chloro-Z group. This combination helps preserve side-chain integrity during iterative assembly, supporting the preparation of lysine-containing peptides and protected intermediates that can be carried forward to later steps with controlled functional-group availability.
2. Protected Peptide Intermediate Synthesis
Boc-Lys(2-chloro-Z)-OSu is commonly selected for preparing protected peptide intermediates and building blocks used in solution-phase or convergent peptide strategies. The reagent's Boc protection on the alpha-amino group and the side-chain 2-chloro-Z protection align with downstream deprotection and coupling sequences, enabling controlled exposure of reactive sites only when needed. In medicinal chemistry and process development settings, this reagent format is frequently used to generate defined lysine-containing fragments that can be condensed with other protected segments to build larger peptide structures without premature side-chain reactivity.
3. Amide-Linked Conjugate Building
Boc-Lys(2-chloro-Z)-OSu is also used as a coupling reagent to form amide-linked conjugates where a lysine-derived, side-chain-protected amide linkage is required as an intermediate. Chemical biology and biomaterials groups often employ this activated ester approach to attach lysine-containing fragments to amine-functionalized scaffolds while keeping the lysine side chain protected for subsequent steps. The OSu activation supports practical coupling to primary amines under standard amide-forming conditions, yielding well-defined protected conjugation intermediates suitable for later functionalization or controlled deprotection.
4. Pharmaceutical Intermediate Development
Boc-Lys(2-chloro-Z)-OSu is relevant to pharmaceutical intermediate development when lysine-protected, activated building blocks are needed for scalable synthesis of peptide-like or lysine-containing structures. Process chemists and intermediate developers use OSu-activated amino acid derivatives to streamline formation of specific amide bonds while maintaining protecting-group patterns that support predictable downstream transformations. The reagent's protected lysine framework helps maintain structural fidelity across multi-step routes, making it a practical choice for constructing defined intermediates used in custom synthesis of peptide-based drug candidates and related research materials.
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