Azido-PEG3-O-NHS ester

 CAS No.: 2110448-98-9  Cat No.: BP-501180  Purity: 98% 4.5  

Azido-PEG3-O-NHS ester is a heterobifunctional polyethylene glycol linker featuring a terminal azide group for bioorthogonal “click” conjugation and a succinimidyl carbonate for efficient coupling to primary amines on proteins, peptides, or amine-functionalized ligands. The PEG3 chain provides a short, flexible spacer that helps reduce steric interference and can improve the accessibility of both the reactive handles during PROTAC assembly. In targeted protein degradation workflows, this linker is commonly used to attach one PROTAC module (e.g., an amine-bearing warhead or scaffold) via activated-carbonate aminolysis to form a carbamate, while preserving the azide for subsequent conjugation to a complementary component (e.g., an alkyne-bearing partner) to generate well-defined, modular constructs. Its dual reactivity and spacer properties make it valuable for preparing PROTACs and related degraders where controlled linkage chemistry and efficient, site-specific module joining are critical for reproducible degradation performance.

Azido-PEG3-O-NHS ester

Structure of 2110448-98-9

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Category
PROTAC Linker
Molecular Formula
C₁₃H₂₀N₄O₈
Molecular Weight
360.32

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

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Popular Publications Citing BOC Sciences Products
Purity
98%
Storage
Please store the product under the recommended conditions in the Certificate of Analysis.
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Room temperature in continental US; may vary elsewhere.
IUPACName
2-[2-[2-(2-azidoethoxy)ethoxy]ethoxy]ethyl (2,5-dioxopyrrolidin-1-yl) carbonate
Synonyms
Azido-PEG3-succinimidyl carbonate
InChI Key
RIGURCMIYKOKGN-UHFFFAOYSA-N
InChI
InChI=1S/C13H20N4O8/c14-16-15-3-4-21-5-6-22-7-8-23-9-10-24-13(20)25-17-11(18)1-2-12(17)19/h1-10H2
SMILES
C1CC(=O)N(C1=O)OC(=O)OCCOCCOCCOCCN=[N+]=[N-]
1. Photochemically-Mediated, Nickel-Catalyzed Synthesis of N-(Hetero)aryl Sulfamate Esters
J Miles Blackburn, Anastasia L Gant Kanegusuku, Georgia E Scott, Jennifer L Roizen Org Lett. 2019 Sep 6;21(17):7049-7054.doi: 10.1021/acs.orglett.9b02621.Epub 2019 Aug 22.
A general method is described for the coupling of (hetero)aryl bromides with O-alkyl sulfamate esters. The protocol relies on catalytic amounts of nickel and photoexcitable iridium complexes and proceeds under visible light irradiation at ambient temperature. This technology engages a broad range of simple and complex O-alkyl sulfamate ester substrates under mild conditions. Furthermore, it is possible to avoid undesirable N-alkylation, which was found to plague palladium-based protocols for N-arylation of O-alkyl sulfamate esters. These investigations represent the first use of sulfamate esters as nucleophiles in transition metal-catalyzed C-N coupling processes.

Azido-PEG3-O-NHS ester is a polyethylene glycol (PEG)-based bifunctional linker designed for building PROTACs and related targeted protein degradation constructs. It combines a succinimidyl carbonate handle for efficient carbamate formation with a terminal azide group for orthogonal bioorthogonal conjugation. Key advantages include water-compatible PEG spacing that can improve linker flexibility and conjugate solubility, enabling modular assembly of ligands under mild conditions. Detailed structural and reactivity considerations are provided below.

Structure: The linker is a PEG chain bearing a succinimidyl carbonate for amine coupling and a terminal azide for click-type functionalization. It contains ether linkages within the PEG backbone, an activated carbonate, and an organic azide, yielding a polar, water-compatible scaffold suitable for conjugation.

Reactivity: The succinimidyl carbonate reacts with primary amines to form stable carbamate linkages via nucleophilic substitution at the carbonate carbonyl, typically using aqueous or mixed aqueous buffers at controlled pH. The azide enables strain-promoted or copper-catalyzed azide–alkyne cycloaddition for subsequent attachment of complementary partners. Common approaches use inert atmosphere when needed, with standard click-compatible solvents and purification to remove excess reagents.

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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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