Key Documents

View All Documentation

929379

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

Name: Opto-thalidomide-O-acetamide-C4-NH2 hydrochloride
Brand: ALDRICH

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

Select a Size

Change View

About This Item

Empirical Formula (Hill Notation):

C₂₉H₃₁N₅O₁₂ · xHCl

Molecular Weight:

641.58 (free base basis)

MDL number:

MFCD34704574

UNSPSC Code:

12352101

NACRES:

NA.22

Technical Service

Need help? Our team of experienced scientists is here for you.

Let Us Assist

Properties

ligand

thalidomide

Quality Segment

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

InChI

1S/C29H31N5O12.ClH/c1-43-21-12-16(19(34(41)42)13-22(21)44-2)14-46-29(40)33-24(36)9-8-18(27(33)38)32-26(37)17-6-5-7-20(25(17)28(32)39)45-15-23(35)31-11-4-3-10-30;/h5-7,12-13,18H,3-4,8-11,14-15,30H2,1-2H3,(H,31,35);1H

InChI key

SEKXAIYNMUPUDC-UHFFFAOYSA-N

Description

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

GHS08,GHS07

signalword

Warning

hcodes

H302,H361d

pcodes

P202 - P264 - P270 - P280 - P301 + P312 - P308 + P313

Hazard Classifications

Acute Tox. 4 Oral - Repr. 2

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c