Fmoc-Val-Cit-PAB is a modular peptide linker containing valine, citrulline, and a para-aminobenzyl segment for triggered release studies. Researchers use it to examine enzymatic activation, spacer flexibility, and controlled cleavage pathways. The construct aids design of responsive biomolecular assemblies. Its Fmoc-protection ensures stable incorporation in solid-phase synthesis.
CAT No: R2261
CAS No:159858-22-7
Synonyms/Alias:Fmoc-Val-Cit-PAB;Fmoc-Val-Cit-PAB-OH;159858-22-7;Fmoc-Val-Cit-PAB (GMP);L-Ornithinamide, N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-valyl-N5-(aminocarbonyl)-N-[4-(hydroxymethyl)phenyl]-;(9H-fluoren-9-yl)methyl ((S)-1-(((S)-1-((4-(hydroxymethyl)phenyl)amino)-1-oxo-5-ureidopentan-2-yl)amino)-3-methyl-1-oxobutan-2-yl)carbamate;9H-fluoren-9-ylmethyl N-[(2S)-1-[[(2S)-5-(carbamoylamino)-1-[4-(hydroxymethyl)anilino]-1-oxopentan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]carbamate;MFCD22417106;(9H-fluoren-9-yl)methyl N-[(1S)-1-{[(1S)-4-(carbamoylamino)-1-{[4-(hydroxymethyl)phenyl]carbamoyl}butyl]carbamoyl}-2-methylpropyl]carbamate;N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-L-valyl-N5-(aminocarbonyl)-N-[4-(hydroxymethyl)phenyl]-L-ornithinamide;ADC linker;9H-fluoren-9-ylmethyl N-[(1S)-1-{[(1S)-4-(carbamoylamino)-1-{[4-(hydroxymethyl)phenyl]carbamoyl}butyl]carbamoyl}-2-methylpropyl]carbamate;N-((9H-Fluoren-9-ylmethoxy)carbonyl)-L-valyl-N5-(aminocarbonyl)-N-(4-(hydroxymethyl)phenyl)-L-ornithinamide;SCHEMBL10066102;DALMAZHDNFCDRP-VMPREFPWSA-N;C33H39N5O6;DTXSID001109558;BCP13071;EX-A3308;HY-19318G;s6688;AKOS027326641;CS-5170;AS-74932;BP-23219;DA-48525;FF176695;HY-19318;CS-0899148;F1223;C70024;892-869-5;N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-valyl-N~5~-carbamoyl-N-[4-(hydroxymethyl)phenyl]-L-ornithinamide;N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-valyl-N5-carbamoyl-N-[4-(hydroxymethyl)phenyl]-L-ornithinamide;
Fmoc-Val-Cit-PAB is a synthetic peptide-based compound that plays a pivotal role in the development of advanced bioconjugation strategies, particularly in the design of cleavable linkers for targeted drug delivery systems. Structurally, it combines an N-terminal Fmoc-protected valine-citrulline dipeptide with a para-aminobenzyl (PAB) spacer, enabling site-specific cleavage under defined enzymatic conditions. The modular architecture and well-characterized cleavage profile of this linker system have made it highly relevant for researchers focusing on the controlled release of payloads in complex biological environments. Its unique properties have positioned it as a critical tool in the synthesis of antibody-drug conjugates (ADCs), prodrugs, and related peptide-functionalized biotherapeutics, supporting both basic research and translational applications in chemical biology.
Antibody-Drug Conjugate (ADC) Synthesis: Fmoc-Val-Cit-PAB is widely utilized as a cleavable linker in the construction of antibody-drug conjugates, where precise control over drug release is essential. The valine-citrulline dipeptide sequence is specifically recognized and cleaved by cathepsin B and related lysosomal proteases, which are often upregulated in targeted cellular compartments. Upon enzymatic cleavage, the PAB spacer undergoes self-immolation, ensuring efficient and predictable release of the cytotoxic payload. This selective cleavage mechanism allows for high specificity in drug delivery, minimizing off-target effects and enhancing the therapeutic index of ADCs under investigation.
Peptide Synthesis and Linker Engineering: In solid-phase peptide synthesis (SPPS), the Fmoc-Val-Cit-PAB motif is incorporated as a functional linker, providing a versatile platform for the attachment of various payloads, including small molecules, fluorophores, and peptides. Its Fmoc protection facilitates orthogonal deprotection strategies, enabling stepwise assembly of complex constructs. Researchers leverage this linker to design and optimize peptide-drug conjugates and multifunctional probes, benefiting from its stability during synthesis and predictable cleavage properties in downstream applications.
Enzymatic Cleavage Studies: The compound serves as a model substrate for investigating protease-specific cleavage events, particularly those mediated by cathepsin B and related lysosomal enzymes. By incorporating Fmoc-Val-Cit-PAB into synthetic constructs, scientists can systematically evaluate the kinetics and selectivity of enzymatic hydrolysis, providing insights into protease activity in various biological matrices. These studies are instrumental in validating linker designs for controlled release and in optimizing bioconjugate performance in preclinical research.
Payload Release Mechanism Characterization: Researchers employ Fmoc-Val-Cit-PAB linkers to study the self-immolative elimination process that follows protease-mediated cleavage. The PAB moiety, upon enzymatic release of the dipeptide, undergoes a rapid intramolecular rearrangement, facilitating the liberation of attached payloads. Detailed characterization of this process informs the rational design of next-generation linker systems, supporting efforts to fine-tune drug release kinetics and improve the safety profiles of bioconjugates.
Chemical Biology and Probe Development: The modular design of this linker system enables its integration into a wide range of chemical biology tools, including activity-based probes, imaging agents, and targeted delivery vehicles. By exploiting the enzyme-sensitive cleavage and the self-immolative characteristics of the PAB spacer, scientists can engineer probes that are selectively activated in defined cellular environments. These capabilities expand the utility of Fmoc-Val-Cit-PAB beyond drug conjugation, supporting innovative approaches in cell tracking, protease profiling, and the study of dynamic biological processes at the molecular level.
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