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920908

(S,R,S)-VL285 Phenol

Synonym(s):

(2S,4R)-4-Hydroxy-N-(2-hydroxy-4-(4-methylthiazol-5-yl)benzyl)-1-((S)-3-methyl-2-(1-oxoisoindolin-2-yl)butanoyl)pyrrolidine-2-carboxamide, VHL E3 ligase ligand for PROTAC® research

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About This Item

Empirical Formula (Hill Notation):
C29H32N4O5S
CAS Number:
1448188-69-9
Molecular Weight:
548.65
UNSPSC Code:
12352200
NACRES:
NA.22
MDL number:
MFCD31746640
Form:
solid
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ligand

VL285 phenol

Quality Level

100

form

solid

reaction suitability

reagent type: ligand

functional group

amine

storage temp.

2-8°C

SMILES string

O=C([C@@H]1C[C@@H](O)CN1C([C@H](C(C)C)N2CC(C=CC=C3)=C3C2=O)=O)NCC4=CC=C(C5=C(C)N=CS5)C=C4O

InChI

1S/C29H32N4O5S/c1-16(2)25(33-13-20-6-4-5-7-22(20)28(33)37)29(38)32-14-21(34)11-23(32)27(36)30-12-19-9-8-18(10-24(19)35)26-17(3)31-15-39-26/h4-10,15-16,21,23,25,34-35H,11-14H2,1-3H3,(H,30,36)/t21-,23+,25+/m1/s1

InChI key

KNZQRBRUYSXXRG-VTZPFEBOSA-N

Application

(S,R,S)-VL285 Phenol is a ligand used in the recruitment of the von Hippel-Lindau (VHL) protein for targeted protein degradation and PROTAC (proteolysis-targeting chimeras) technology, providing an alternative to the widely used VH032 (901490).

(S,R,S)-VL285 Phenol-linker conjugates are also available for synthesis of degraders. Browse our full offering of degrader building blocks that streamlines the synthesis of degrader libraries.

Other Notes

Technology Spotlight: Degrader Building Blocks for Targeted Protein Degradation

Portal: Building PROTAC® Degraders for Targeted Protein Degradation

HaloPROTACS: Use of Small Molecule PROTACs to Induce Degradation of HaloTag Fusion Proteins

Systematic exploration of different E3 ubiquitin ligases: an approach towards potent and selective CDK6 degraders

Design, synthesis and biological evaluation of Proteolysis Targeting Chimeras (PROTACs) as a BTK degraders with improved pharmacokinetic properties

Differential PROTAC substrate specificity dictated by orientation of recruited E3 ligase

Legal Information

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

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Articles

Degrader Building Blocks for Targeted Protein Degradation

Protein Degrader Building Blocks are a collection of crosslinker-E3 ligand conjugates with a pendant functional group for covalent linkage to a target ligand.

Saul Jaime-Figueroa et al.
Bioorganic & medicinal chemistry letters, 30(3), 126877-126877 (2019-12-28)
A new series of Proteolysis Targeting Chimeras (PROTACs) targeting Bruton's Tyrosine Kinase (BTK) was synthesized, with the goal of improving the pharmacokinetic properties of our previously reported PROTAC, MT802. We recently described the ability of MT802 to induce degradation of
Dennis L Buckley et al.
ACS chemical biology, 10(8), 1831-1837 (2015-06-13)
Small molecule-induced protein degradation is an attractive strategy for the development of chemical probes. One method for inducing targeted protein degradation involves the use of PROTACs, heterobifunctional molecules that can recruit specific E3 ligases to a desired protein of interest.

Global Trade Item Number

SKUGTIN
920908-100MG04065266173680