Lipoamide-PEG11-Mal

Name: Lipoamide-PEG11-Mal
Brand: BOC Sciences
Rating: 5 (1 reviews)

Cat No.: BP-501928

Purity: ≥95% 4.5

Lipoamide-PEG11-Mal is a heterobifunctional PROTAC linker featuring a lipoamide-derived 1,2-dithiolane/disulfide-containing amide anchor conjugated to a long, hydrophilic polyethylene glycol chain terminated with a maleimide group. The PEG segment provides an extended, flexible spacer that improves solubility and spatial reach between the two conjugation partners, while the maleimide enables selective coupling to thiol-containing ligands (for example, cysteine- or thiol-functionalized warheads) via stable thioether bond formation under mild conditions. In PROTAC design, this linker is used to connect or distance a targeting moiety from an E3 ligase recruiting element, thereby tuning effective ternary complex geometry and reducing steric clashes that can limit ubiquitination efficiency. Its lipoamide anchor supports robust attachment strategies commonly employed in modular targeted degradation workflows, making it valuable for constructing and optimizing degraders that require long-range conjugation and reliable, chemoselective linkage.

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Category

PROTAC Linker

Molecular Formula

C39H69N3O15S2

Molecular Weight

884.11

Related CAS

2767245-00-9 (polymer) 1334172-73-4 ((3R)-polymer)

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

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Purity

≥95%

Storage

Store at 2-8°C

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Room temperature in continental US; may vary elsewhere.

IUPACName

N-(2-(2-(2-(2-(2-(2-(2-(2-(2-(2-(2-(2-(3-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)propanamido)ethoxy)ethoxy)ethoxy)ethoxy)ethoxy)ethoxy)ethoxy)ethoxy)ethoxy)ethoxy)ethoxy)ethyl)-5-(1,2-dithiolan-3-yl)pentanamide

Synonyms

LA-PEG11-NH-Mal; Lipoamide-PEG11-NH-Mal; MAL-PEG11-Lipoamide; MAL-dPEG(R)11-Lipoamide; N-(39-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)-37-oxo-3,6,9,12,15,18,21,24,27,30,33-undecaoxa-36-azanonatriacontyl)-5-(1,2-dithiolan-3-yl)pentanamide; 1H-Pyrrole-1-propanamide, N-[41-(1,2-dithiolan-3-yl)-37-oxo-3,6,9,12,15,18,21,24,27,30,33-undecaoxa-36-azahentetracont-1-yl]-2,5-dihydro-2,5-dioxo-; N-[39-(2,5-Dioxo-2,5-dihydro-1H-pyrrol-1-yl)-37-oxo-3,6,9,12,15,18,21,24,27,30,33-undecaoxa-36-azanonatriacont-1-yl]-5-(1,2-dithiolan-3-yl)pentanamide

Boiling Point

934.9±65.0°C at 760 mmHg

Density

1.2±0.1 g/cm3

InChI Key

MCLHFRMIEQEYEN-UHFFFAOYSA-N

InChI

InChI=1S/C39H69N3O15S2/c43-36(4-2-1-3-35-8-34-58-59-35)40-9-12-47-14-16-49-18-20-51-22-24-53-26-28-55-30-32-57-33-31-56-29-27-54-25-23-52-21-19-50-17-15-48-13-10-41-37(44)7-11-42-38(45)5-6-39(42)46/h5-6,35H,1-4,7-34H2,(H,40,43)(H,41,44)

SMILES

C1CSSC1CCCCC(=O)NCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCNC(=O)CCN2C(=O)C=CC2=O

This PROTAC linker, Lipoamide-PEG11-Mal, is designed to connect a lipoamide-based handle to a maleimide electrophile, enabling efficient assembly of targeted protein degraders. Its PEG-based spacer provides conformational flexibility and improved solubility, supporting productive ternary complex formation. The maleimide functionality supports selective conjugation to thiol-bearing ligands, while the lipoamide motif can be used to integrate redox-relevant linkages in degrader design. Detailed structural and reactivity considerations follow below.

Structure: The linker contains a PEG-derived hydrophilic chain that separates functional termini, improving aqueous compatibility. A maleimide group provides an activated alkene for thiol addition, while a lipoamide unit offers a thioamide-bearing motif. The molecule is stabilized by heteroatom-rich linkages and exhibits amphiphilic character.

Reactivity: Maleimides typically undergo rapid Michael-type addition with thiols under mildly basic aqueous conditions, forming a stable thioether conjugate. For PROTAC construction, thiol-functionalized ligands (or thiol-releasing precursors) are reacted with the maleimide end to install the connection. Commonly used solvents include aqueous buffers with compatible cosolvents, and reactions are often performed at controlled pH to minimize maleimide hydrolysis.

Stock concentration: *

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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