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929379

Sigma-Aldrich

Opto-thalidomide-O-acetamide-C4-NH2 hydrochloride

Synonym(s):

4,5-Dimethoxy-2-nitrobenzyl 3-(4-(2-((4-aminobutyl)amino)-2-oxoethoxy)-1,3-dioxoisoindolin-2-yl)-2,6-dioxopiperidine-1-carboxylate hydrochloride

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About This Item

Empirical Formula (Hill Notation):
C29H31N5O12 · xHCl
Molecular Weight:
641.58 (free base basis)
UNSPSC Code:
12352101
NACRES:
NA.22

ligand

thalidomide

Quality Level

100

form

powder

functional group

amine

storage temp.

2-8°C

SMILES string

COC1=CC(COC(N2C(CCC(N3C(C4=CC=CC(OCC(NCCCCN)=O)=C4C3=O)=O)C2=O)=O)=O)=C(C=C1OC)[N+]([O-])=O.Cl

Application

Protein degrader building block Opto-thalidomide-O-acetamide-C4-NH2 hydrochloride enables the synthesis of molecules for light-induced targeted protein degradation and PROTAC® (proteolysis-targeting chimeras) research. This conjugate contains a Cereblon (CRBN) recruiting ligand, a rigid 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 degrader, 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 degrader libraries that feature variation in crosslinker length, composition, and E3 ligase ligand.

Technology Spotlight: Degrader Building Blocks for Targeted Protein Degradation

Protein Degrader Building Blocks

Other Notes

Targeted Protein Degradation by Small Molecules

Light-induced control of protein destruction by opto-PROTAC

Small-Molecule PROTACS: New Approaches to Protein Degradation

Targeted Protein Degradation: from Chemical Biology to Drug Discovery

Impact of linker length on the activity of PROTACs

Legal Information

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

Pictograms

Health hazardExclamation mark
GHS08,GHS07

Signal Word

Warning

Hazard Statements

H302,H361d

Hazard Classifications

Acute Tox. 4 Oral - Repr. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Daniel P Bondeson et al.
Annual review of pharmacology and toxicology, 57, 107-123 (2016-10-13)
Protein homeostasis networks are highly regulated systems responsible for maintaining the health and productivity of cells. Whereas therapeutics have been developed to disrupt protein homeostasis, more recently identified techniques have been used to repurpose homeostatic networks to effect degradation of

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