m-PEG5-phosphonic acid ethyl ester

 CAS No.: 1807512-42-0  Cat No.: BP-501385  Purity: ≥95% 4.5  

m-PEG5-phosphonic acid ethyl ester is a heterobifunctional PEG-based linker featuring a methoxy-terminated PEG5 chain and a diethyl phosphonate group, providing a chemically versatile handle for PROTAC assembly. The PEG segment contributes water solubility and conformational flexibility, helping to reduce steric interference between the target-binding ligand and the E3 ligase-recruiting moiety while promoting productive ternary complex formation. The diethyl phosphonate mainly serves as a protected phosphonate motif and can be de-esterified to a more polar phosphonic acid; it is not a standard direct covalent-coupling handle. In targeted protein degradation research, this linker is valuable for tuning linker length, hydrophilicity, and spatial orientation, which are key determinants of cellular uptake, stability, and degradation potency.

m-PEG5-phosphonic acid ethyl ester

Structure of 1807512-42-0

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Category
PROTAC Linker
Molecular Formula
C15H33O8P
Molecular Weight
372.39

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

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Purity
≥95%
Solubility
Soluble in DMSO
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
1-[2-[2-[2-(2-diethoxyphosphorylethoxy)ethoxy]ethoxy]ethoxy]-2-methoxyethane
Synonyms
Diethyl 2,5,8,11,14-pentaoxahexadecan-16-ylphosphonate; Phosphonic acid, P-3,6,9,12,15-pentaoxahexadec-1-yl-, diethyl ester
Boiling Point
437.8±40.0°C at 760 mmHg
Density
1.1±0.1 g/cm3
InChI Key
COMONJQWUBCUJE-UHFFFAOYSA-N
InChI
InChI=1S/C15H33O8P/c1-4-22-24(16,23-5-2)15-14-21-13-12-20-11-10-19-9-8-18-7-6-17-3/h4-15H2,1-3H3
SMILES
CCOP(=O)(CCOCCOCCOCCOCCOC)OCC

m-PEG5-phosphonic acid ethyl ester is a PEG-based linker designed to support targeted protein degradation (PROTAC) architectures by providing aqueous compatibility, conformational flexibility, and a chemically addressable phosphonate handle. Its ether-rich chain can help tune linker length and solvation, while the phosphonate functionality enables robust coupling strategies to assemble bifunctional degraders. The detailed Structure and Reactivity parameters are provided below.

Structure: This linker contains a methoxy-terminated polyethylene glycol (PEG) ether backbone and a phosphonate group protected as a diethyl ester. The structure features ether linkages and a fully esterified phosphonate P–O framework, yielding a polar scaffold that can provide ionizable phosphonic-acid functionality after dealkylation.

Reactivity: The diethyl phosphonate ester can be converted to the corresponding phosphonic acid under standard phosphonate-ester dealkylation conditions used in linker chemistry. After appropriate dealkylation, the resulting phosphonic acid can be further derivatized using conditions selected for phosphonate chemistry and partner compatibility. Mild aqueous/organic solvent mixtures are typically employed to maintain PEG integrity and minimize side reactions.

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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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