Mal-amido-PEG9-NH-Boc

 CAS No.: 2182602-20-4  Cat No.: BP-501340 4.5  

Mal-amido-PEG9-NH-Boc is a heterobifunctional polyethylene glycol (PEG) linker bearing a maleimide-thioether reactive group and a terminal Boc-protected amine. Structurally, it comprises a PEG chain of nine ethylene glycol units that provides aqueous solubility and conformational flexibility, coupled to a maleimide moiety for selective conjugation to nucleophilic thiols (e.g., cysteine-containing ligands or engineered proteins) via Michael addition, forming a stable thioether linkage. The Boc-protected amine enables subsequent coupling or further functionalization after deprotection, allowing integration into PROTAC architectures where two ligands must be positioned to support efficient ternary complex formation with an E3 ligase and the target protein. In targeted protein degradation research, PEG-based linkers like this help tune spatial distance and reduce steric penalties, improving conjugate stability and facilitating systematic structure–activity optimization during PROTAC synthesis and evaluation.

Mal-amido-PEG9-NH-Boc

Structure of 2182602-20-4

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PROTAC Linker
Molecular Formula
C₃₂H₅₇N₃O₁₄
Molecular Weight
707.81

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

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IUPACName
tert-butyl N-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[3-(2,5-dioxopyrrol-1-yl)propanoylamino]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethyl]carbamate
InChI Key
VHRNVZPRNZMLFJ-UHFFFAOYSA-N
InChI
InChI=1S/C32H57N3O14/c1-32(2,3)49-31(39)34-8-11-41-13-15-43-17-19-45-21-23-47-25-27-48-26-24-46-22-20-44-18-16-42-14-12-40-10-7-33-28(36)6-9-35-29(37)4-5-30(35)38/h4-5H,6-27H2,1-3H3,(H,33,36)(H,34,39)
SMILES
CC(C)(C)OC(=O)NCCOCCOCCOCCOCCOCCOCCOCCOCCOCCNC(=O)CCN1C(=O)C=CC1=O

Mal-amido-PEG9-NH-Boc is a polyethylene glycol–based PROTAC linker designed to connect ligand modules while promoting solubility and conformational flexibility in targeted protein degradation constructs. Its maleimide motif and protected amine enable controlled synthetic assembly of bifunctional degraders, supporting efficient formation of stable conjugates for subsequent cellular evaluation. The following sections describe its structure and practical reactivity considerations in PROTAC workflows.

Structure: The linker contains a PEG chain providing hydrophilicity and segmental flexibility, coupled to a maleimide-derived connection and a terminal Boc-protected amine. It features amide linkages and carbamate protection, with heteroatom-rich segments that support hydrogen bonding and improved aqueous compatibility.

Reactivity: The Boc-protected amine is suitable for stepwise coupling after deprotection under standard acid-mediated conditions used for Boc removal. The resulting free amine can then participate in amide-bond formation with activated carboxylic acids or activated ester intermediates, while the maleimide can undergo thiol-selective Michael addition. Linker assembly is typically performed using coupling reagents commonly employed in peptide/bioconjugation chemistry, in polar aprotic solvents, to minimize side reactions and preserve labile functionalities during PROTAC synthesis.

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It is commonly abbreviated as: C1V1 = C2V2

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Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
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