VH 101, phenol

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Description: Hydroxyl functionalized VHL ligand
Chemical Name: (2S,4R)-1-((S)-2-(1-Fluorocyclopropane-1-carboxamido)-3,3-dimethylbutanoyl)-4-hydroxy-N-(2-hydroxy-4-(4-methylthiazol-5-yl)benzyl)pyrrolidine-2-carboxamide
Purity: ≥98% (HPLC)
Literature (1)

Biological Activity for VH 101, phenol

VH 101, phenol is a functionalized von-Hippel-Lindau protein ligand (VHL) for PROTAC® research and development; incorporates an E3 ligase ligand with terminal hydroxyl ready for conjugation to a target protein ligand. Part of a range of functionalized tool molecules for PROTAC R&D.

Please contact us for SD files of our available Degrader Building Blocks.

PROTAC® is a registered trademark of Arvinas Operations, Inc., and is used under license.

Licensing Information

Sold under licence from the University of Dundee.

Usage Guidelines for VH 101, phenol

This product is provided for use in onward chemistry. Suitable solvents can be used.

Technical Data for VH 101, phenol

M. Wt 532.63
Formula C26H33FN4O5S
Storage Store at +4°C
Purity ≥98% (HPLC)
CAS Number 2306193-99-5
PubChem ID 137628614
Smiles CC1=C(SC=N1)C2=CC=C(CNC([C@@H]3C[C@@H](O)CN3C([C@@H](NC(C4(CC4)F)=O)C(C)(C)C)=O)=O)C(O)=C2

The technical data provided above is for guidance only. For batch specific data refer to the Certificate of Analysis.

Tocris products are intended for laboratory research use only, unless stated otherwise.

Product Datasheets for VH 101, phenol

Certificate of Analysis / Product Datasheet
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References for VH 101, phenol

References are publications that support the biological activity of the product.

Zoppi et al (2019) Iterative design and optimization of initially inactive Proteolysis Targeting Chimeras (PROTACs) identify VZ185 as a potent, fast, and selective Von Hippel-Lindau (VHL) based dual degrader probe of BRD9 and BRD7. J.Med.Chem. 62 699 PMID: 30540463

Girardini et al (2019) Cereblon versus VHL: hijacking E3 ligases against each other using PROTACs. Bioorg.Med.Chem. 27 2466 PMID: 30826187

Farnaby et al (2019) BAF complex vulnerabilities in cancer demonstrated via structure-based PROTAC design. Nat.Chem.Biol. 15 672 PMID: 31178587

Maniaci et al (2017) Homo-PROTACs: bivalent small-molecule dimerizers of the VHL E3 ubiquitin ligase to induce self-degradation. Nat.Commun. 8 830 PMID: 29018234

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Literature in this Area

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Targeted Protein Degradation Poster

Targeted Protein Degradation Poster

Degraders (e.g. PROTACs) are bifunctional small molecules, that harness the Ubiquitin Proteasome System (UPS) to selectively degrade target proteins within cells. They consist of three covalently linked components: an E3 ubiquitin ligase ligand, a linker and a ligand for the target protein of interest. Authored in-house, this poster outlines the generation of a toolbox of building blocks for the development of Degraders. The characteristics and selection of each of these components are discussed. Presented at EFMC 2018, Ljubljana, Slovenia