Tetrazine-Ph-PEG5-NHS ester

 CAS No.: 1682653-80-0  Cat No.: BP-501097  Purity: 95% 4.5  

Tetrazine-Ph-PEG5-NHS ester is a bifunctional PEG-based linker designed for PROTAC and related targeted degradation workflows that require robust, site-selective conjugation. Structurally, it combines a tetrazine moiety for rapid inverse-electron-demand Diels–Alder reactivity with a phenyl spacer and a five-unit poly(ethylene glycol) chain terminating in an N-hydroxysuccinimide (NHS) ester. The NHS ester enables efficient coupling to primary amines on lysine residues or engineered tags of targeting ligands (e.g., small-molecule binders or peptides), while the tetrazine group can subsequently react with complementary trans-cyclooctene or strained-alkene partners to form a stable conjugation under mild conditions. This architecture helps tune linker length and hydrophilicity, improving solubility and reducing non-specific interactions, while providing modular assembly of multi-component degraders. The reagent is therefore valuable for constructing well-defined PROTACs and for optimizing conjugation strategies in targeted protein degradation research.

Tetrazine-Ph-PEG5-NHS ester

Structure of 1682653-80-0

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Category
PROTAC Linker
Molecular Formula
C₂₇H₃₆N₆O₁₀
Molecular Weight
604.61

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

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Purity
95%
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
(2,5-dioxopyrrolidin-1-yl) 3-[2-[2-[2-[2-[3-oxo-3-[[4-(1,2,4,5-tetrazin-3-yl)phenyl]methylamino]propoxy]ethoxy]ethoxy]ethoxy]ethoxy]propanoate
Synonyms
Tetrazine-PEG5-NHS ester
InChI Key
DUPHIQYIPUTDJS-UHFFFAOYSA-N
InChI
InChI=1S/C27H36N6O10/c34-23(28-19-21-1-3-22(4-2-21)27-31-29-20-30-32-27)7-9-38-11-13-40-15-17-42-18-16-41-14-12-39-10-8-26(37)43-33-24(35)5-6-25(33)36/h1-4,20H,5-19H2,(H,28,34)
SMILES
C1CC(=O)N(C1=O)OC(=O)CCOCCOCCOCCOCCOCCC(=O)NCC2=CC=C(C=C2)C3=NN=CN=N3

Tetrazine-Ph-PEG5-NHS ester is a PEG-based linker engineered for modular PROTAC construction, enabling efficient conjugation of targeting ligands to tetrazine-bearing handles for bioorthogonal assembly. Its flexible polyethylene glycol scaffold improves solubility and conformational freedom, while the NHS ester supports rapid amide formation under standard bioconjugation conditions. This product is well suited for researchers designing targeted protein degradation workflows, where subsequent steps require reliable, controllable linkage chemistry; detailed structural and reactivity considerations are provided below.

Structure: The linker combines a tetrazine functional group with a phenyl spacer and a polyethylene glycol chain terminating in an N-hydroxysuccinimide ester. It contains aromatic rings, ether linkages within the PEG backbone, and an activated carboxyl-derived amide-forming moiety, supporting aqueous compatibility and stable conjugation chemistry.

Reactivity: The NHS ester reacts with primary amines to form amide bonds via nucleophilic acyl substitution, typically using mildly basic conditions to promote amine deprotonation while preserving tetrazine integrity. Common solvents include aqueous buffers compatible with NHS chemistry, often with controlled organic co-solvents when needed. After amide coupling, tetrazine-containing intermediates can participate in bioorthogonal ligation with suitable partners under conditions that maintain tetrazine reactivity 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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