(2S,4R)-N-[(1S)-1-(4-fluorophenyl)-3-(methylamino)-3-oxopropyl]-4-hydroxy-1-[(2R)-3-methyl-2-(3-methyl-1,2-oxazol-5-yl)butanoyl]pyrrolidine-2-carboxamide
CAS No.: 2581824-91-9
Cat No.: BP-200056
4.5 
(2S,4R)-N-[(1S)-1-(4-fluorophenyl)-3-(methylamino)-3-oxopropyl]-4-hydroxy-1-[(2R)-3-methyl-2-(3-methyl-1,2-oxazol-5-yl)butanoyl]pyrrolidine-2-carboxamide is a selective VHL (von Hippel-Lindau) E3 ligase ligand, specifically engineered for the development of PROTACs (Proteolysis Targeting Chimeras). Classified as an E3 Ligase Ligand, this compound serves as a key building block in synthetically linking target protein binders to the cellular ubiquitin-proteasome system, enabling targeted protein degradation. Frequently used in targeted protein degradation research, this ligand facilitates the design of small-molecule degraders that exploit the VHL pathway, expanding the toolkit for addressing previously undruggable targets. Its optimized structure and affinity for VHL make it an essential reagent for scientists working in chemical biology, drug discovery, and next-generation therapeutics.
![(2S,4R)-N-[(1S)-1-(4-fluorophenyl)-3-(methylamino)-3-oxopropyl]-4-hydroxy-1-[(2R)-3-methyl-2-(3-methyl-1,2-oxazol-5-yl)butanoyl]pyrrolidine-2-carboxamide](https://resource.bocsci.com/structure/2581824-91-9.gif)
Structure of 2581824-91-9
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* For research and manufacturing use only. Not for human or clinical use.
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Background Introduction
(2S,4R)-N-[(1S)-1-(4-fluorophenyl)-3-(methylamino)-3-oxopropyl]-4-hydroxy-1-[(2R)-3-methyl-2-(3-methyl-1,2-oxazol-5-yl)butanoyl]pyrrolidine-2-carboxamide is a highly specialized ligand designed to engage the E3 ubiquitin ligase VHL (von Hippel-Lindau). VHL-based ligands are integral tools in targeted protein degradation (TPD) strategies, particularly in the synthesis of PROTACs (Proteolysis Targeting Chimeras), where they enable precise recruitment of the VHL E3 ligase complex.
Mechanism
This compound specifically binds to the VHL E3 ligase, facilitating the recruitment of the VCB (VHL-Cullin 2-Elongin B/C) ligase complex to the target protein. When incorporated as the E3 ligase ligand portion of a PROTAC, it creates a proximity-induced interaction between the target protein and the E3 ligase machinery. This drives polyubiquitination of the target protein, marking it for rapid recognition and degradation via the 26S proteasome. The presence of tailored chemical groups such as the 4-fluorophenyl and 3-methyl-1,2-oxazol moieties optimizes ligand affinity, selectivity, and solubility for efficient PROTAC design.
Applications
This VHL ligand is a valuable scaffold for creating bifunctional molecules used in PROTAC-based research and drug discovery. Applications include:
• Synthesis of VHL-recruiting PROTACs for targeted protein degradation• Development of chemical probes to interrogate undruggable proteins
• Screening and optimization in structure-activity relationship (SAR) studies for degrader projects
• Pharmaceutical research, including preclinical validation of novel degraders
• Tool compound development for studying cellular protein homeostasis
• Consistent batch-to-batch reproducibility with complete QC documentation
• Supplied with COA, MSDS, and analytical data for traceability
• Reliable global shipping with stability-guaranteed packaging
• Dedicated technical support and optional custom synthesis service
• Demonstrates strong binding affinity to CRBN, VHL, or other E3 ligases
• Enables stable E3 ligase recruitment for targeted protein degradation
• Highly selective VHL E3 ligase ligand enables targeted protein degradation applications.
• Optimized structure for efficient incorporation into VHL-based PROTACs, enhancing research in drug discovery.
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
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