Phthalimide-PEG4-MPDM-OH

Name: Phthalimide-PEG4-MPDM-OH
Brand: BOC Sciences
Rating: 5 (1 reviews)

Cat No.: BP-501909 4.5

Phthalimide-PEG4-MPDM-OH is a bifunctional polyethylene glycol linker featuring a phthalimide moiety connected through a short PEG chain to an MPDM-derived handle terminated with a free hydroxyl. Structurally, the PEG segment provides a flexible, hydrophilic spacer that can reduce steric clashes between the warhead-binding ligand and the E3 ligase–recruiting element, while maintaining sufficient reach for productive ternary complex formation. In PROTAC architectures, the phthalimide group is used to engage the CRBN E3 ligase via the phthalimide–CRBN recognition module, and the hydroxyl-functionalized MPDM portion serves as a conjugation point for attachment to a target-binding ligand or for further derivatization. This linker is valuable for researchers optimizing linker length, polarity, and spatial orientation to improve ubiquitination efficiency and targeted protein degradation potency, particularly when flexible spacing is required to balance binding affinity and degradation kinetics.

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Category

PROTAC Linker

Molecular Formula

C₂₂H₃₂N₂O₇

Molecular Weight

436.50

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

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Storage

Please store the product under the recommended conditions in the Certificate of Analysis.

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Room temperature in continental US; may vary elsewhere.

IUPACName

2-[2-[2-[2-[2-[(3R,5S)-5-(hydroxymethyl)-1-methylpyrrolidin-3-yl]oxyethoxy]ethoxy]ethoxy]ethyl]isoindole-1,3-dione

InChI Key

VYZQARMSNCUHEH-ZWKOTPCHSA-N

InChI

InChI=1S/C22H32N2O7/c1-23-15-18(14-17(23)16-25)31-13-12-30-11-10-29-9-8-28-7-6-24-21(26)19-4-2-3-5-20(19)22(24)27/h2-5,17-18,25H,6-16H2,1H3/t17-,18+/m0/s1

SMILES

CN1CC(CC1CO)OCCOCCOCCOCCN2C(=O)C3=CC=CC=C3C2=O

Phthalimide-PEG4-MPDM-OH is a multifunctional PROTAC linker designed to connect a phthalimide-based ligand to an MPDM-derived handle while providing a flexible polyethylene glycol spacer for productive ternary complex formation. Its ether-rich, hydrophilic character can improve solubility and reduce non-specific interactions, supporting efficient targeted protein degradation workflows. The detailed structure and practical reactivity considerations for PROTAC assembly are provided below.

Structure: The linker contains a phthalimide moiety conjugated to a PEG-based chain and an MPDM-derived segment terminating in a carboxylic acid. It features ester/amide-compatible functional groups, ether linkages within the PEG region, and a terminal hydroxyl-bearing acid functionality suitable for coupling chemistry. Overall, it is flexible and polar.

Reactivity: The terminal carboxylic acid enables standard PROTAC linker coupling through activation to reactive intermediates, followed by amide or related bond formation with complementary amine-bearing partners under mild organic conditions. Common approaches use carbodiimide-type activators with additives to suppress side reactions, typically in polar aprotic solvents. Mechanistically, activation forms an acyl intermediate that is trapped by the nucleophile to yield stable conjugates suitable for PROTAC synthesis.

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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