920894

(S,R,S)-VL285 Phenol-PEG₂-NH₂ hydrochloride

• Synonym(s): (2R,4S)-N-(2-(2-(2-(2-Aminoethoxy)ethoxy)ethoxy)-4-(4-methylthiazol-5-yl)benzyl)-4-hydroxy-1-((R)-3-methyl-2-(1-oxoisoindolin-2-yl)butanoyl)pyrrolidine-2-carboxamide hydrochloride, Crosslinker−E3 Ligase ligand conjugate, VHL protein degrader building block for PROTAC^® research
• Empirical Formula (Hill Notation): C₃₅H₄₅N₅O₇S · xHCl
• Molecular Weight: 679.83 (free base basis)
• MDL number: MFCD34549912
• UNSPSC Code: 12352200
• NACRES: NA.22
• eCl@ss: 32150313
• Form: solid

Properties

• ligand: VL285 phenol
• Quality Segment: 100
• form: solid
• reaction suitability: reactivity: carboxyl reactive, reagent type: ligand-linker conjugate
• technique(s): targeted protein degradation: suitable
• 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=C4OCCOCCOCCN.Cl
• InChI: 1S/C35H45N5O7S.ClH/c1-22(2)31(40-19-26-6-4-5-7-28(26)34(40)43)35(44)39-20-27(41)17-29(39)33(42)37-18-25-9-8-24(32-23(3)38-21-48-32)16-30(25)47-15-14-46-13-12-45-11-10-36;/h4-9,16,21-22,27,29,31,41H,10-15,17-20,36H2,1-3H3,(H,37,42);1H/t27-,29+,31+;/m0./s1
• InChI key: RJXJVEJULBIZRR-YSQLAWOQSA-N

Description

Application

Protein degrader building block (S,R,S)-VL285 Phenol-PEG₂-NH₂ hydrochloride enables the synthesis of molecules for targeted protein degradation and PROTAC (proteolysis-targeting chimeras) technology. This conjugate contains a von Hippel-Lindau (VHL)-recruiting ligand with alternative exit vector from the widely used VH032 (901490), a PEG linker, and a pendant amine for reactivity with a carboxylic acid on the target ligand. Because even slight alterations in ligands and crosslinkers can affect ternary complex formation between the target, E3 ligase, and PROTAC, many analogs are prepared to screen for optimal target degradation. When used with other protein degrader building blocks with a terminal amine, parallel synthesis can be used to more quickly generate PROTAC libraries that feature variation in crosslinker length, composition, and E3 ligase ligand.

Automate your VHL-PEG based PROTACs with Synple Automated Synthesis Platform (SYNPLE-SC002)

Other Notes

Technology Spotlight: Degrader Building Blocks for Targeted Protein Degradation

Portal: Building PROTAC^® Degraders for Targeted Protein Degradation

Targeted Protein Degradation by Small Molecules

Targeted Protein Degradation: from Chemical Biology to Drug Discovery

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

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

Safety Information

• Storage Class: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point (°F): Not applicable
• Flash Point (°C): Not applicable