Name: Thalidomide-linker 2
Brand: BOC Sciences
Rating: 5 (1 reviews)

Size

Price

Stock

Quantity

$--

In stock

Purity

≥98%

ShelfLife

2 years

Storage

-20°C

Synonyms

N-(14-Amino-3,6,9,12-tetraoxatetradec-1-yl)-2-[[2-(2,6-dioxo-3-piperidinyl)-2,3-dihydro-1,3-dioxo-1H-isoindol-4-yl]oxy]acetamide hydrochloride

InChI Key

YHQOQBFOLKFJJN-UHFFFAOYSA-N

InChI

InChI=1S/C25H34N4O10.ClH/c26-6-8-35-10-12-37-14-15-38-13-11-36-9-7-27-21(31)16-39-19-3-1-2-17-22(19)25(34)29(24(17)33)18-4-5-20(30)28-23(18)32;/h1-3,18H,4-16,26H2,(H,27,31)(H,28,30,32);1H

Canonical SMILES

C1CC(=O)NC(=O)C1N2C(=O)C3=C(C2=O)C(=CC=C3)OCC(=O)NCCOCCOCCOCCOCCN.Cl

Background Introduction

Thalidomide-linker 2 is a specialized E3 ligase ligand-linker conjugate designed for use in targeted protein degradation research, specifically within the context of PROTAC (Proteolysis Targeting Chimera) technology. As a derivative of thalidomide, Thalidomide-linker 2 enables efficient recruitment of the cereblon (CRBN) E3 ubiquitin ligase, which plays a critical role in mediating ubiquitination and proteasomal degradation of target proteins. This product is structurally optimized with a functionalized linker, facilitating the rational design of bifunctional PROTAC molecules.

Mechanism

Thalidomide-linker 2 operates by serving as the E3 ligase-recruiting moiety in the molecular architecture of PROTACs. The thalidomide portion binds selectively to the CRBN E3 ligase, while the chemical linker provides a reactive handle for conjugation to a ligand specific for a protein of interest. Once incorporated into a PROTAC molecule, Thalidomide-linker 2 orchestrates the spatial proximity between the E3 ligase and the designated target protein. This induced proximity promotes the ubiquitination of the target protein by CRBN, marking it for subsequent recognition and degradation by the cellular proteasome system.

Applications

Thalidomide-linker 2 is widely used in the development of next-generation targeted protein degradation therapeutics, chemical biology research, and drug discovery pipelines. Its key applications include: (1) Synthesis of PROTACs targeting a diverse array of disease-relevant proteins, including kinases, transcription factors, and epigenetic regulators; (2) Mechanistic studies investigating the efficiency and selectivity of CRBN-mediated protein degradation; and (3) Exploration of structure-activity relationships (SAR) to enhance the pharmacological properties of PROTAC molecules. Employing Thalidomide-linker 2 enables researchers to accelerate the generation of effective and specific protein degraders, driving innovation in personalized medicine and biotechnology.

• Versatile thalidomide-based structure enables efficient CRBN E3 ligase recruitment in PROTAC development.
• Pre-installed linker design streamlines synthetic workflows for rapid assembly of novel PROTAC molecules.

1. 2'-O-[2-(amino)-2-oxoethyl] oligonucleotides

Thazha P Prakash, Andrew M Kawasaki, Elena A Lesnik, Stephen R Owens, Muthiah Manoharan Org Lett. 2003 Feb 20;5(4):403-6.doi: 10.1021/ol027131k.

[structure: see text] Oligonucleotides with novel modifications, 2'-O-[2-(amino)-2-oxoethyl] (2'-O-NAc), 2'-O-[2-(methylamino)-2-oxoethyl] (2'-O-NMAc), 2'-O-[2-(dimethylamino)-2-oxoethyl] (2'-O-DMAc), and 2'-O-[2-[[2-(dimethylamino)ethyl]amino]-2-oxoethyl] (2'-O-DMAEAc), have been synthesized. These modified oligonucleotides exhibit high binding affinity to complementary RNA (and not to DNA) and considerably enhance the nuclease stability of oligonucleotides with t(1/2) > 24 h.

Stock concentration: *

Desired final volume: *

Desired concentration: *

* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C₁V₁ = C₂V₂