Azido-PEG10-NHS ester

Name: Azido-PEG10-NHS ester
Brand: BOC Sciences
Rating: 5 (1 reviews)

Cat No.: BP-501968

Purity: ≥95% 4.5

Azido-PEG10-NHS ester is a heterobifunctional polyethylene glycol linker designed for PROTAC and targeted protein degradation workflows, featuring an NHS ester for amide-bond formation with primary amines and a terminal azide handle for orthogonal conjugation via azide–alkyne cycloaddition or related click chemistries. The PEG chain provides a flexible, hydrophilic spacer that can reduce steric interference between the two PROTAC-relevant modules (typically a targeting ligand and an E3 ligase binder), while improving solubility and helping maintain productive ternary complex formation. In experimental design, the NHS ester enables rapid coupling to amine-bearing components under standard acylation conditions, and the azide functionality allows subsequent attachment to complementary partners bearing an alkyne or other azide-reactive group, enabling modular assembly and late-stage functionalization. This linker is valuable for constructing degraders with controlled linker length and chemistry, facilitating systematic structure–activity studies and optimization of degradation potency and selectivity.

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Category

PROTAC Linker

Molecular Formula

C27H48N4O14

Molecular Weight

652.70

Related CAS

1108750-59-9 (polymer)

Appearance

Pale Yellow or Colorless Oily Matter

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

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Popular Publications Citing BOC Sciences Products

Purity

≥95%

Solubility

Soluble in DCM, DMF, DMSO

Appearance

Pale Yellow or Colorless Oily Matter

Storage

Store at 2-8°C

Shipping

Room temperature in continental US; may vary elsewhere.

IUPACName

(2,5-dioxopyrrolidin-1-yl) 3-[2-[2-[2-[2-[2-[2-[2-[2-[2-(2-azidoethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]propanoate

Synonyms

Azido-PEG10-CH2CO2-NHS; N3-PEG10-C2-NHS ester; N3-PEG10-CH2CH2COONHS Ester; 1-[(1-Azido-33-oxo-3,6,9,12,15,18,21,24,27,30-decaoxatritriacontan-33-yl)oxy]-2,5-pyrrolidinedione; 2,5-Pyrrolidinedione, 1-[(33-azido-1-oxo-4,7,10,13,16,19,22,25,28,31-decaoxatritriacont-1-yl)oxy]-

InChI Key

XMNPNFSCYDZTJD-UHFFFAOYSA-N

InChI

InChI=1S/C27H48N4O14/c28-30-29-4-6-36-8-10-38-12-14-40-16-18-42-20-22-44-24-23-43-21-19-41-17-15-39-13-11-37-9-7-35-5-3-27(34)45-31-25(32)1-2-26(31)33/h1-24H2

SMILES

C1CC(=O)N(C1=O)OC(=O)CCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCN=[N+]=[N-]

1. Fast-Acting Antibacterial, Self-Deactivating Polyionene Esters

Christian Krumm, Sylvia Trump, Lena Benski, Jens Wilken, Franziska Oberhaus, Manfred Köller, Joerg C Tiller ACS Appl Mater Interfaces. 2020 May 13;12(19):21201-21209.doi: 10.1021/acsami.9b19313.Epub 2020 Jan 9.

Biocidal compounds that quickly kill bacterial cells and are then deactivated in the surrounding without causing environmental problems are of great current interest. Here, we present new biodegradable antibacterial polymers based on polyionenes with inserted ester functions (PBI esters). The polymers are prepared by polycondensation reaction of 1,4-dibromobutene and different tertiary diaminodiesters. The resulting PBI esters are antibacterially active against a wide range of bacterial strains and were found to quickly kill these cells within 1 to 10 min. Because of hydrolysis of the ester groups, the PBI esters are degraded and deactivated in aqueous media. The degradation rate depends on the backbone structure and the pH. The structure of the polymers also controls the deactivation mechanism. While the more hydrophilic polymers require hydrolyses of only 19 to 30% of the ester groups to become practically inactive, the more hydrophobic PBI esters require up to 85% hydrolysis to achieve the same result. Thus, depending on the environmental conditions and the chemical nature, the PBI esters can be active for only 20 min or for at least one week.

Azido-PEG10-NHS ester is a bifunctional PEG-based linker designed for modular PROTAC assembly, enabling efficient conjugation to amine-bearing ligands via an NHS ester while retaining a terminal azide handle for orthogonal “click” coupling. Its PEG scaffold provides favorable solubility and conformational flexibility, supporting productive ternary complex formation. The following points describe the linker’s structure and the practical reactivity considerations for constructing PROTACs using this reagent.

Structure: The molecule contains a terminal azide group attached to a polyethylene glycol chain and an N-hydroxysuccinimide ester at the other end. It features stable ether linkages within the PEG backbone, an activated carboxylate for acyl transfer, and a reactive azide for bioorthogonal cycloaddition.

Reactivity: The NHS ester reacts with primary amines under mild, aqueous or mixed aqueous conditions to form stable amide bonds, typically using buffering to maintain NHS reactivity. The terminal azide is compatible with copper-catalyzed azide–alkyne cycloaddition or strain-promoted azide–alkyne cycloaddition, enabling orthogonal installation of the complementary partner. Common solvents include buffered water or alcohol-containing mixtures, with copper catalysts used only when compatible with sensitive ligands.

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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