Boc-Lys(2-picolinoyl)-OH is a Boc-protected lysine derivative bearing a side-chain 2-picolinoyl acyl substituent on the ε-amino group, classifying it as a modified, protected amino acid suitable for peptide-related chemistry. The α-amino group is protected as a Boc carbamate while the carboxyl group is present as a free acid, and the lysine backbone features a primary side-chain nitrogen that is converted to an amide bearing a pyridine-containing 2-picolinoyl moiety, with stereochemistry not specified in the name. In synthesis, this protected amino acid functions as a controlled building block for stepwise peptide assembly where the Boc group supports chemoselective coupling at the α-position and the 2-picolinoyl side-chain modification provides a defined functional handle for studies of metal coordination, side-chain reactivity control, or structure-activity investigations of lysine analogs.
CAT No: CP26256
CAS No:122532-80-3
Synonyms/Alias:Boc-Lys(2-Picolinoyl)-OH;122532-80-3;AC1M156R;ZINC2573513;6404AH;(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-6-(pyridine-2-carbonylamino)hexanoicAcid;A-8533;Na-t-Butoxycarbonyl-Ne-(2-picolinoyl)-L-lysine
Boc-Lys(2-picolinoyl)-OH is a Boc-protected lysine derivative bearing a 2-picolinoyl acyl group on the side-chain ε-amino functionality, providing a protected and chemically differentiated lysine building block for peptide and peptidomimetic synthesis. The Boc group supports standard N-protection strategies for controlled coupling chemistry, while the picolinoyl substituent offers an additional handle for downstream transformations and side-chain functional differentiation during assembly. This reagent is typically selected when a lysine residue with a specific side-chain protection pattern is required to manage reactivity and improve synthetic control in complex sequences.
1. Solid-Phase Peptide Synthesis
Boc-Lys(2-picolinoyl)-OH is used by peptide synthesis groups to introduce a lysine residue with an orthogonally differentiated side-chain protection pattern, supporting stepwise assembly on resin. Researchers commonly employ this building block when they need to control lysine ε-amino reactivity relative to other side chains, enabling reliable coupling and minimizing undesired side reactions during multi-residue sequence construction. The Boc-protected α-amino functionality aligns with widely used peptide synthesis workflows, while the 2-picolinoyl side-chain acyl group provides a distinct protection environment that can be leveraged in downstream peptide modification or segment strategies.
2. Side-Chain Protected Lysine Intermediates
Boc-Lys(2-picolinoyl)-OH is frequently used in medicinal chemistry and peptide-chemistry development as a defined lysine intermediate for preparing modified peptide segments and analogs. Custom peptide manufacturers and process-focused synthetic chemists select this reagent when the lysine side chain must remain masked in a controlled manner through early stages of synthesis, yet still allow planned downstream processing to reach a target structure. The picolinoyl substituent supports a side-chain-specific protection scheme that helps maintain sequence integrity while enabling later conversion to the desired lysine functionality for library generation, SAR studies, or complex peptide assembly.
3. Peptide Library And Analog Synthesis
Boc-Lys(2-picolinoyl)-OH supports peptide library construction where lysine side-chain identity and protection state must be consistent across analogs to ensure comparable coupling performance and purification behavior. In structure-activity relationship (SAR) workflows, researchers often incorporate this protected lysine building block to generate series of peptides that differ in other positions while maintaining a standardized lysine side-chain protection pattern. This approach is particularly useful for teams building peptidomimetic scaffolds or sequence variants where side-chain chemistry must be held constant until the library is advanced to the next functionalization stage.
4. Pharmaceutical Intermediate Development
Boc-Lys(2-picolinoyl)-OH is also used as a specialty intermediate in the development of peptide-based pharmaceutical candidates and related peptidomimetic structures, where controlled protection of lysine is required during intermediate manufacturing. Process development chemists value this building block for its defined functional group pattern, which can simplify planning of downstream transformations and help maintain reproducibility across batches of protected peptide fragments. The combination of Boc α-amino protection with a 2-picolinoyl ε-amino acyl protection supports practical synthetic staging for producing well-defined intermediates used in later coupling, modification, or final assembly steps.
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