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Merck
CN

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
MDL number:
MFCD31746640
UNSPSC Code:
12352200
NACRES:
NA.22

Key Documents

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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

Related Categories

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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
0000279675
0000279675
0000208961
0000205443
0000205443

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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
Christian Steinebach et al.
Chemical science, 11(13), 3474-3486 (2020-11-03)
Cyclin-dependent kinase 6 (CDK6) is an important regulator of the cell cycle. Together with CDK4, it phosphorylates and inactivates retinoblastoma (Rb) protein. In tumour cells, CDK6 is frequently upregulated and CDK4/6 kinase inhibitors like palbociclib possess high activity in breast
Blake E Smith et al.
Nature communications, 10(1), 131-131 (2019-01-12)
PROteolysis-TArgeting Chimeras (PROTACs) are hetero-bifunctional molecules that recruit an E3 ubiquitin ligase to a given substrate protein resulting in its targeted degradation. Many potent PROTACs with specificity for dissimilar targets have been developed; however, the factors governing degradation selectivity within
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.

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.

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