Boc-L-Lys(Boc)-ONp is a protected amino acid derivative of lysine in which the α-amino group is protected as a Boc carbamate and the ε-amino side chain is further protected as a Boc group, forming a bis-Boc lysine scaffold. The molecule also contains a carboxyl group converted to an ONp ester (p-nitrophenyl ester), which bears an activated ester functionality while retaining the lysine backbone stereochemistry indicated by the L designation. As an amino acid ester suitable for peptide coupling, it provides an electrophilic carboxyl handle for forming amide bonds and is commonly used in the preparation of protected peptide intermediates and related lysine-containing peptide derivatives under conditions that accommodate Boc-protected amines.
CAT No: CP25677
CAS No:2592-19-0
Chemical Name:N-alpha-N-epsilon-di-t-Butyloxycarbonyl-L-lysine p-nitrophenyl ester
Boc-L-Lys(Boc)-ONp is a protected lysine derivative featuring an N-terminal Boc group and a Boc-protected side-chain, supplied as the p-nitrophenyl ester (ONp) that serves as an activated carboxylate for peptide coupling. This structure is designed to enable efficient amide bond formation under peptide synthesis conditions while maintaining orthogonal protection patterns typical of protected amino acid building blocks. Researchers select this ONp ester form when they need a robust electrophile for incorporating lysine segments into protected peptide intermediates and related synthetic workflows.
1. Peptide Coupling Reagent
Boc-L-Lys(Boc)-ONp is used as an activated lysine building block for assembling protected peptide segments in solution-phase peptide synthesis and custom peptide intermediate production. The p-nitrophenyl ester activation provides a reactive carboxylate equivalent that reacts with appropriate amine partners to form the next peptide bond while retaining the Boc protections on both the α-amino group and the lysine side chain. This makes the reagent particularly relevant for workflows that require lysine-containing sequences where side-chain protection must be preserved through coupling and subsequent intermediate handling.
2. Protected Lysine Segment Synthesis
Boc-L-Lys(Boc)-ONp supports the preparation of lysine-rich peptide fragments and branched or multi-lysine architectures where controlled side-chain functionality is essential. Synthetic chemists and peptide manufacturing teams commonly use this activated, doubly Boc-protected lysine to build defined peptide intermediates that can later be further elaborated, condensed, or purified without exposing the ε-amino group prematurely. The Boc-on-lysine design helps maintain compatibility with standard peptide-workup and purification steps, while the ONp ester form streamlines conversion into the corresponding amide-linked product in the coupling stage.
3. Pharmaceutical Intermediate Assembly
Boc-L-Lys(Boc)-ONp is applied in the development of protected peptide-like intermediates used in medicinal chemistry programs and peptide-based lead optimization. Teams preparing lysine-containing linkers, protected oligopeptide fragments, or final coupling-ready intermediates rely on the activated ONp ester to integrate lysine units efficiently into larger synthetic sequences. The reagent's dual Boc protection pattern supports downstream transformations by keeping lysine functionality masked until the synthesis reaches the deprotection or final assembly stage, aligning with common industrial intermediate manufacturing workflows.
4. Orthogonally Protected Peptide Building Block
Boc-L-Lys(Boc)-ONp is frequently selected when a protected lysine unit must remain fully protected during iterative assembly steps, including repeated coupling and intermediate purification cycles. The presence of Boc on both the α-amino and ε-amino positions provides a consistent protection strategy for lysine incorporation, reducing the risk of side reactions from unprotected amines during peptide fragment construction. In practice, peptide chemists use this activated ester to generate defined, Boc-protected lysine-containing intermediates that can be carried forward into further elongation or final functionalization with predictable protection behavior.
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