Thalidomide-5-(PEG2-amine)

Name: Thalidomide-5-(PEG2-amine)
Brand: BOC Sciences
Rating: 5 (1 reviews)

CAS No.: 2550398-08-6

Cat No.: BP-502138 4.5

Thalidomide-5-(PEG2-amine) is a bifunctional PROTAC linker building block that retains the thalidomide-derived cereblon-binding pharmacophore while introducing a short, flexible polyethylene glycol (PEG) spacer terminating in a primary amine. Structurally, the thalidomide moiety serves as the CRBN/E3-ligase recruiter, while the terminal primary amine provides a defined attachment handle for coupling to an additional linker fragment or target-binding ligand in a PROTAC construct. The PEG segment increases conformational flexibility and aqueous compatibility, helping to reduce steric clashes and to maintain productive ternary complex formation between the target protein, the PROTAC, and cereblon. For targeted protein degradation research, this reagent is valuable for rapid synthesis of thalidomide-based degraders, enabling systematic evaluation of linker length and attachment chemistry while preserving the core E3 engagement motif.

Structure of 2550398-08-6

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PROTAC Linker

Molecular Formula

C20H24N4O7

Molecular Weight

432.43

* For research and manufacturing use only. Not for human or clinical use.

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IUPACName

N-[2-[2-(2-aminoethoxy)ethoxy]ethyl]-2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindole-5-carboxamide

Synonyms

N-[2-[2-(2-aminoethoxy)ethoxy]ethyl]-2-(2,6-dioxo-3-piperidyl)-1,3-dioxo-isoindoline-5-carboxamide

InChI Key

JHPUXMJZJYXENI-UHFFFAOYSA-N

InChI

InChI=1S/C20H24N4O7/c21-5-7-30-9-10-31-8-6-22-17(26)12-1-2-13-14(11-12)20(29)24(19(13)28)15-3-4-16(25)23-18(15)27/h1-2,11,15H,3-10,21H2,(H,22,26)(H,23,25,27)

SMILES

C1CC(=O)NC(=O)C1N2C(=O)C3=C(C2=O)C=C(C=C3)C(=O)NCCOCCOCCN

Thalidomide-5-(PEG2-amine) is a PEG-amine functionalized thalidomide-derived linker designed for assembling targeted protein degradation (PROTAC) constructs. Its ether-rich PEG segment provides conformational flexibility and improved solubility, while the terminal amine enables robust conjugation to a wide range of warheads or coupling handles. This linker supports efficient formation of PROTAC architectures that recruit an E3 ligase via the thalidomide moiety. Detailed structural and reactivity considerations are provided below.

Structure: The molecule contains a thalidomide core connected through a linker position to a short polyethylene glycol chain terminating in a primary amine. Its framework features multiple heteroatoms (including oxygen and nitrogen) and aromatic and lactam-like functionalities, with ether linkages contributing to polarity and hydration-friendly behavior.

Reactivity: The terminal primary amine is suitable for standard PROTAC coupling strategies such as amide-bond formation with activated carboxylic acids or carboxylate derivatives, as well as urea or carbamate linkages when complementary activated electrophiles are used. Conjugations are typically performed under mild base or coupling conditions in polar aprotic solvents with moisture control. Mechanistically, nucleophilic acyl substitution or related condensation pathways enable stable linker installation, and common coupling reagents can be selected to match the electrophile on the partner warhead.

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* 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