Val-Lys(Boc)-PAB incorporates a protected lysine that assists in controlled peptide elongation. The para-aminobenzyl component provides a versatile linker for cleavage studies in synthetic biology. Valine contributes hydrophobic balance, shaping secondary structure preferences. Applications extend to prodrug design models, enzymatic cleavage mapping, and modular peptide assembly.
CAT No: R2314
CAS No:1432969-86-2
Synonyms/Alias:Val-Lys(Boc)-PAB;1432969-86-2;PAB-Val-Lys-Boc;Val-Lys(Boc)-PAB?;tert-butyl N-[(5S)-5-[[(2S)-2-amino-3-methylbutanoyl]amino]-6-[4-(hydroxymethyl)anilino]-6-oxohexyl]carbamate;tert-Butyl ((S)-5-((S)-2-amino-3-methylbutanamido)-6-((4-(hydroxymethyl)phenyl)amino)-6-oxohexyl)carbamate;SCHEMBL16424839;EX-A5040;DA-58949;HY-138651;CS-0161755;F73273;
Val-Lys(Boc)-PAB is a synthetic peptide building block comprising valine and lysine residues, with the lysine side chain protected by a tert-butyloxycarbonyl (Boc) group and para-aminobenzyl (PAB) functionality. As a bifunctional reagent, it is designed for advanced peptide synthesis and conjugation strategies, offering unique orthogonality and functional versatility. Its chemical architecture provides both a protected amine and a reactive aromatic moiety, making it valuable for constructing complex peptide architectures and facilitating site-specific modifications. Researchers in peptide chemistry and chemical biology frequently utilize such protected derivatives to achieve precise control over molecular assembly and post-synthetic modifications.
Peptide Synthesis: In solid-phase peptide synthesis (SPPS), Val-Lys(Boc)-PAB serves as a specialized amino acid derivative for introducing lysine residues with orthogonally protected side chains. The Boc group shields the ε-amino group of lysine from undesired reactions during chain elongation, enabling selective deprotection and subsequent functionalization at later synthetic stages. This property is particularly advantageous when constructing branched peptides, cyclic peptides, or multi-functionalized peptide scaffolds, as it allows for controlled incorporation of additional chemical handles without compromising the integrity of the peptide backbone.
Conjugation Chemistry: The PAB moiety within this building block provides a handle for further chemical conjugation. This aromatic group can act as a linker or spacer, facilitating the attachment of a wide range of molecules, including fluorescent probes, affinity tags, or other bioactive moieties. The unique reactivity of the PAB group supports the development of peptide-drug conjugates, targeted delivery systems, and advanced diagnostic reagents. Its presence enables chemoselective modification strategies that are essential for the creation of multifunctional bioconjugates in research settings.
Enzyme Substrate Design: Utilization of Val-Lys(Boc)-PAB is common in the design of synthetic substrates for proteolytic enzyme assays. The protected lysine residue and the PAB group together allow for the generation of substrates with tunable cleavage sites and reporter functionalities. Such substrates are invaluable for profiling protease specificity, studying enzyme kinetics, and screening for inhibitors in biochemical research. The modularity of this building block supports the rapid generation of tailored assay reagents for high-throughput screening platforms.
Peptide-Drug Linker Development: The combination of orthogonally protected lysine and the PAB moiety makes this compound suitable for the construction of cleavable linkers in peptide-drug conjugates. The PAB group is frequently employed as a self-immolative spacer that, upon enzymatic or chemical cleavage, facilitates the controlled release of attached therapeutic or diagnostic payloads. This application is particularly relevant in the development of targeted delivery systems where precise control over payload release is critical for optimizing bioactivity and minimizing off-target effects in experimental models.
Analytical Tool Creation: Researchers leverage the unique structural features of Val-Lys(Boc)-PAB to develop analytical tools for peptide mapping, quantification, and characterization. Its orthogonal protection scheme allows for stepwise deprotection and labeling, supporting the synthesis of peptides with site-specific isotopic or fluorescent labels. These labeled peptides are essential for mass spectrometry-based quantitation, imaging studies, or mechanistic investigations in proteomics and chemical biology. The compound's versatility thus underpins a broad range of analytical workflows requiring high specificity and modularity in peptide modification.
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