Lipoamido-PEG4-acid

 CAS No.: 1314378-10-3  Cat No.: BP-500743  Purity: ≥95% 4.5  

Lipoamido-PEG4-acid is a PEG-based linker featuring a terminal carboxylic acid for conjugation and a lipoamido-bearing segment that provides a hydrophobic handle alongside the hydrophilic PEG chain. The PEG4 length offers conformational flexibility and improved aqueous solubility, helping to reduce steric interference between the two functional ends of a PROTAC construct. In targeted protein degradation designs, this linker can be used to connect an E3 ligase ligand or other binding moiety to a second component, while the lipoamido element can support stable attachment strategies and modulate local microenvironment around the recruited complex. The terminal acid enables straightforward coupling to amine- or hydrazide-functional partners using standard peptide-coupling or activated-carboxyl chemistries. As a modular, water-compatible PROTAC linker, it is valuable for systematically tuning linker length, polarity, and attachment geometry to optimize ternary complex formation and degradation potency in experimental studies.

Lipoamido-PEG4-acid

Structure of 1314378-10-3

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Category
PROTAC Linker
Molecular Formula
C19H35NO7S2
Molecular Weight
453.61
Related CAS
1334172-69-8 (R-isomer) 1334172-71-2 (polymer)
Appearance
Light Yellow or White Solid

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

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Purity
≥95%
Solubility
Soluble in DMSO
Appearance
Light Yellow or White Solid
Storage
Store at 2-8°C for short term (days to weeks) or -20°C for long term (months to years)
Shipping
Room temperature in continental US; may vary elsewhere.
IUPACName
3-(2-(2-(2-(2-(5-(1,2-dithiolan-3-yl)pentanamido)ethoxy)ethoxy)ethoxy)ethoxy)propanoic acid
Synonyms
Lipoamido-PEG4-CH2CH2COOH; LA-PEG4-COOH; Lipoamido-PEG4-COOH; 3-[2-[2-[2-[2-[5-(dithiolan-3-yl)pentanoylamino]ethoxy]ethoxy]ethoxy]ethoxy]propanoic acid; 4,7,10,13-Tetraoxa-16-azaheneicosanoic acid, 21-(1,2-dithiolan-3-yl)-17-oxo-; 21-(1,2-Dithiolan-3-yl)-17-oxo-4,7,10,13-tetraoxa-16-azahenicosan-1-oic acid
Density
1.2±0.1 g/cm3
InChI Key
QJFPDZROPSGMGV-UHFFFAOYSA-N
InChI
InChI=1S/C19H35NO7S2/c21-18(4-2-1-3-17-6-16-28-29-17)20-7-9-25-11-13-27-15-14-26-12-10-24-8-5-19(22)23/h17H,1-16H2,(H,20,21)(H,22,23)
SMILES
C1CSSC1CCCCC(=O)NCCOCCOCCOCCOCCC(=O)O

Lipoamido-PEG4-acid is a PEG-based linker designed to connect a lipid-like moiety to a terminal carboxylic acid, enabling flexible spacing and improved conjugation compatibility in targeted protein degradation constructs. Its hydrophilic PEG segment supports solubility and conformational adaptability, while the acid handle facilitates robust amide or ester-forming coupling to ligands used in PROTAC architectures. The detailed structural and reactivity considerations are provided below for researchers planning linker installation and PROTAC assembly.

Structure: The linker contains a PEG chain segment flanked by an amide (lipoamido) linkage and a terminal carboxylic acid. It features stable covalent amide bonds and an acid group capable of forming activated intermediates. The PEG portion imparts hydrophilicity and conformational flexibility, supporting aqueous compatibility in conjugation workflows.

Reactivity: The terminal carboxylic acid is suitable for standard PROTAC linker coupling via amide-bond formation using carboxyl activation reagents (for example, carbodiimides with coupling additives) under controlled base and temperature conditions. Alternatively, acid activation followed by nucleophilic substitution can furnish ester intermediates when desired. These transformations proceed through formation of an activated ester/amide intermediate, typically in polar aprotic solvents, enabling attachment to amine-bearing ligands used for targeted degradation.

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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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