Propargyl-PEG4-O-C1-NHS ester

 CAS No.: 1161883-51-7  Cat No.: BP-501465  Purity: ≥95% 4.5  

Propargyl-PEG4-O-C1-NHS ester is a heterobifunctional polyethylene glycol (PEG) linker designed for PROTAC and targeted protein degradation workflows, combining a terminal propargyl group for bioorthogonal “click” conjugation and an NHS ester for efficient coupling to primary amines on ligands or carrier proteins. Structurally, it consists of a PEG4 chain (short, flexible hydrophilic spacer) linked through an ether linkage to a carbonyl-activated N-hydroxysuccinimide group, enabling formation of stable amide bonds under standard amine-reactive conditions. In PROTAC assembly, the PEG spacer helps tune distance and solubility between the two functional modules, while the propargyl handle allows orthogonal attachment to azide-bearing partners, facilitating modular synthesis and controlled stoichiometry. This linker is valuable for constructing degradation agents where maintaining productive geometry and minimizing steric hindrance are critical for efficient ternary complex formation and subsequent ubiquitin–proteasome pathway engagement.

Propargyl-PEG4-O-C1-NHS ester

Structure of 1161883-51-7

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Category
PROTAC Linker
Molecular Formula
C17H25NO9
Molecular Weight
387.38
Appearance
Pale Yellow Oily Matter

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

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Purity
≥95%
Solubility
Soluble in DCM, DMF, DMSO
Appearance
Pale Yellow Oily Matter
Storage
Store at 2-8°C
Shipping
Room temperature in continental US; may vary elsewhere.
IUPACName
(2,5-dioxopyrrolidin-1-yl) 2-[2-[2-[2-(2-prop-2-ynoxyethoxy)ethoxy]ethoxy]ethoxy]acetate
Synonyms
Propargyl-PEG5-CH2CO2-NHS; 2,5-Dioxopyrrolidin-1-yl 3,6,9,12,15-pentaoxaoctadec-17-ynoate; 3,6,9,12,15-Pentaoxaoctadec-17-ynoic acid, 2,5-dioxo-1-pyrrolidinyl ester; Propargyl-PEG4-CH2COONHS; Propargyl-PEG5-CH2COO-NHS ester; Propargyl-PEG5-CH2COOH NHS Ester; 1-(3,6,9,12,15-Pentaoxaoctadec-17-ynoyloxy)-2,5-pyrrolidinedione; 2,5-Pyrrolidinedione, 1-[(1-oxo-3,6,9,12,15-pentaoxaoctadec-17-yn-1-yl)oxy]-
Boiling Point
486.2±55.0°C at 760 mmHg
Density
1.3±0.1 g/cm3
InChI Key
BNRYRRHZTIDZOR-UHFFFAOYSA-N
InChI
InChI=1S/C17H25NO9/c1-2-5-22-6-7-23-8-9-24-10-11-25-12-13-26-14-17(21)27-18-15(19)3-4-16(18)20/h1H,3-14H2
SMILES
C#CCOCCOCCOCCOCCOCC(=O)ON1C(=O)CCC1=O

Propargyl-PEG4-O-C1-NHS ester is a PEG-based, bifunctional linker designed for constructing PROTACs through orthogonal conjugation. Its NHS ester enables efficient amide-bond formation with primary amines on targeting ligands, while the terminal propargyl group supports subsequent bioorthogonal “click” coupling to complementary partners. This combination improves modular synthesis, linker flexibility, and conjugation control, which are advantageous for assembling targeted protein degradation constructs. Detailed structural and reactivity considerations follow below.

Structure: The linker contains a PEG chain providing hydrophilicity and conformational flexibility, connected through an ether linkage to a terminal propargyl group. An NHS-activated ester is present for acyl transfer to amines, forming stable amide bonds. Overall, it behaves as a reactive, water-compatible conjugation scaffold.

Reactivity: The NHS ester typically reacts with primary amines under mildly basic aqueous or mixed solvent conditions to form amide linkages, often using buffered media to preserve NHS reactivity. The propargyl handle is suitable for copper-catalyzed azide–alkyne cycloaddition or related click chemistries to connect to azide-functional components. Common solvents include aqueous buffers and polar organic cosolvents; catalysts and ligand systems are selected to balance click efficiency and protein/ligand compatibility.

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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 ╳
g/mol
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