Tetrazine-Ph-NHCO-PEG4-NH-Boc

Name: Tetrazine-Ph-NHCO-PEG4-NH-Boc
Brand: BOC Sciences
Rating: 5 (1 reviews)

Cat No.: BP-502085 4.5

Tetrazine-Ph-NHCO-PEG4-NH-Boc is a bifunctional, PEG-based PROTAC linker featuring a tetrazine moiety conjugated through a phenyl spacer to a carbamate/amide sequence and terminated with a Boc-protected amine. The PEG4 segment provides a flexible, hydrophilic tether that can enhance effective reach and reduce steric hindrance between the two PROTAC components during assembly and in-cell proximity. In targeted protein degradation workflows, the tetrazine handle is designed for rapid inverse-electron-demand Diels–Alder ligation with trans-cyclooctene–functionalized partners, enabling efficient, chemoselective coupling of a ligand (e.g., E3 ligase binder) to a second ligand (e.g., target binder) through a defined spacer. The Boc group offers a protected amine for controlled derivatization or subsequent deprotection to introduce additional coupling sites. This linker is valuable for constructing modular, well-tethered PROTACs where reaction selectivity and linker flexibility are critical to achieving productive ternary complex formation.

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Category

PROTAC Linker

Molecular Formula

C₂₅H₃₈N₆O₇

Molecular Weight

534.61

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

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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

tert-butyl N-[2-[2-[2-[2-[3-oxo-3-[[4-(1,2,4,5-tetrazin-3-yl)phenyl]methylamino]propoxy]ethoxy]ethoxy]ethoxy]ethyl]carbamate

InChI Key

ONEPWSXYUDGVRI-UHFFFAOYSA-N

InChI

InChI=1S/C25H38N6O7/c1-25(2,3)38-24(33)26-9-11-35-13-15-37-17-16-36-14-12-34-10-8-22(32)27-18-20-4-6-21(7-5-20)23-30-28-19-29-31-23/h4-7,19H,8-18H2,1-3H3,(H,26,33)(H,27,32)

SMILES

CC(C)(C)OC(=O)NCCOCCOCCOCCOCCC(=O)NCC1=CC=C(C=C1)C2=NN=CN=N2

This PROTAC linker, Tetrazine-Ph-NHCO-PEG4-NH-Boc, is designed to connect a tetrazine-bearing warhead to a protein-binding ligand through a flexible polyethylene glycol spacer and protected amine functionality. Its modular architecture supports efficient assembly of targeted protein degradation constructs and helps tune linker length, solubility, and conformational freedom at the ternary-complex interface. The points below describe its structural features and practical reactivity considerations for PROTAC synthesis in detail.

Structure: The linker contains a tetrazine core connected to a phenyl spacer, followed by an amide (NHCO) and a PEG-based polyether chain, terminating in a protected amine (Boc). Aromatic and heteroaromatic rings, amide linkages, and ether oxygen atoms provide polarity, flexibility, and hydrogen-bonding capability.

Reactivity: Tetrazine functionality is suited to bioorthogonal inverse-electron-demand Diels–Alder ligation with strained dienes (commonly trans-cyclooctene or related cyclooalkenes), enabling rapid conjugation under mild conditions. The Boc-protected amine can be selectively deprotected using standard acidolysis to generate a nucleophilic handle for subsequent coupling. Amide formation typically proceeds via carbodiimide-mediated coupling in appropriate polar solvents, with bases to promote activation and coupling efficiency.

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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