Lipoamido-PEG12-acid

 CAS No.: 2407442-47-9  Cat No.: BP-501179  Purity: ≥95% 4.5  

Lipoamido-PEG12-acid is a PEG-based linker bearing a terminal carboxylic acid and a lipoamide-derived 1,2-dithiolane cyclic disulfide motif, providing a flexible hydrophilic spacer of approximately twelve ethylene glycol units between the conjugation handle and the lipid/amide-adjacent region. In PROTAC and targeted degradation constructs, such PEG linkers are used to tune the spatial relationship and effective reach between the ligand moieties that recruit an E3 ubiquitin ligase and the target-binding warhead, while improving aqueous solubility and reducing nonspecific hydrophobic interactions. The lipoamido cyclic disulfide provides a chemically and redox-relevant motif, while the terminal carboxylic acid is the main direct coupling handle, enabling controlled conjugation to other components through amide-forming or activated-carboxyl chemistries. This linker is valuable for researchers seeking to optimize linker length and polarity to enhance ternary complex formation, improve degradation potency, and maintain favorable physicochemical properties during iterative PROTAC design and structure–activity studies.

Lipoamido-PEG12-acid

Structure of 2407442-47-9

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Category
PROTAC Linker
Molecular Formula
C35H67NO15S2
Molecular Weight
806.03
Related CAS
1334172-71-2 (polymer)
Appearance
White to Orange to Green Powder to Crystal

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

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Purity
≥95%
Appearance
White to Orange to Green Powder to Crystal
Storage
Store at 2-8°C
Shipping
Room temperature in continental US; may vary elsewhere.
IUPACName
3-(2-(2-(2-(2-(2-(2-(2-(2-(2-(2-(2-(2-(5-(1,2-dithiolan-3-yl)pentanamido)ethoxy)ethoxy)ethoxy)ethoxy)ethoxy)ethoxy)ethoxy)ethoxy)ethoxy)ethoxy)ethoxy)ethoxy)propanoic acid
Synonyms
Lipoamido-PEG12-CH2CH2COOH; Lipoamido-PEG12-carboxylic Acid; Lipoamido-dPEG(R)12-acid; 45-(1,2-dithiolan-3-yl)-41-oxo-4,7,10,13,16,19,22,25,28,31,34,37-dodecaoxa-40-azapentatetracontanoic acid; 4,7,10,13,16,19,22,25,28,31,34,37-Dodecaoxa-40-azapentatetracontan-1-oic acid, 45-(1,2-dithiolan-3-yl)-41-oxo-; 3-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[5-(dithiolan-3-yl)pentanoylamino]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]propanoic acid
Density
1.2±0.1 g/cm3
InChI Key
KTDABPXYRAJNFQ-UHFFFAOYSA-N
InChI
InChI=1S/C35H67NO15S2/c37-34(4-2-1-3-33-6-32-52-53-33)36-7-9-41-11-13-43-15-17-45-19-21-47-23-25-49-27-29-51-31-30-50-28-26-48-24-22-46-20-18-44-16-14-42-12-10-40-8-5-35(38)39/h33H,1-32H2,(H,36,37)(H,38,39)
SMILES
C1CSSC1CCCCC(=O)NCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCC(=O)O

Lipoamido-PEG12-acid is a PEG-based PROTAC linker designed to connect targeting ligands while providing a flexible, water-compatible spacer that can improve effective ternary complex formation. Its lipoamido motif supports robust conjugation strategies to common ligand chemotypes, and the terminal carboxylic acid enables reliable coupling to amine-bearing partners. The detailed structural and reactivity considerations for constructing PROTACs are provided below.

Structure: The linker comprises a hydrophilic polyethylene glycol segment coupled to a lipoamido linkage and terminated by a carboxylic acid. It contains ether linkages within the PEG chain, an amide bond in the lipoamido region, and a terminal carboxyl group capable of forming salts or activating for coupling.

Reactivity: The carboxylic acid is suitable for amide-bond formation via activation using standard coupling chemistries (for example, carbodiimide-based systems with an additive such as an N-hydroxysuccinimide derivative). Conjugation to amine-functionalized ligands is typically performed under controlled pH in polar aprotic solvents, proceeding through formation of an activated ester followed by nucleophilic acyl substitution. The PEG chain generally confers good solubility, supporting homogeneous reaction conditions.

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Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2

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Tip: Chemical formula is case sensitive. C22H30N4O c22h30n40
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