Methyltetrazine-PEG4-amine

 CAS No.: 1802908-05-9  Cat No.: BP-501445  Purity: 95% 4.5  

Methyltetrazine-PEG4-amine is a heterobifunctional PROTAC linker featuring a methyltetrazine moiety conjugated to a four-unit polyethylene glycol (PEG) chain terminated with a primary amine. The PEG segment provides aqueous solubility and conformational flexibility, while the methyltetrazine group enables rapid inverse-electron-demand Diels–Alder reactivity with strained alkenes/dienophiles such as trans-cyclooctene (TCO) or norbornene used as bioorthogonal handles in targeted protein degradation workflows. The terminal amine allows straightforward coupling to carboxyl-activated ligands or other functionalized fragments, facilitating modular assembly of ternary-complex degraders. In PROTAC design, this linker supports efficient conjugation of the “warhead” and the E3 ligase-binding component (or other targeting elements) while minimizing steric interference through the PEG spacer. It is therefore valuable for researchers optimizing linker length, geometry, and reaction kinetics to improve degradation potency and experimental reproducibility in targeted protein degradation studies.

Methyltetrazine-PEG4-amine

Structure of 1802908-05-9

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Category
PROTAC Linker
Molecular Formula
C₁₇H₂₅N₅O₄
Molecular Weight
363.41

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

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Purity
95%
Solubility
Water, DMSO, DMF, DCM
Storage
Please store the product under the recommended conditions in the Certificate of Analysis.
Shipping
Room temperature in continental US; may vary elsewhere.
IUPACName
2-[2-[2-[2-[4-(6-methyl-1,2,4,5-tetrazin-3-yl)phenoxy]ethoxy]ethoxy]ethoxy]ethanamine
Synonyms
Methyltetrazine-PEG4-amine HCl salt
InChI Key
JOEAATMYJGXMGS-UHFFFAOYSA-N
InChI
InChI=1S/C17H25N5O4/c1-14-19-21-17(22-20-14)15-2-4-16(5-3-15)26-13-12-25-11-10-24-9-8-23-7-6-18/h2-5H,6-13,18H2,1H3
SMILES
CC1=NN=C(N=N1)C2=CC=C(C=C2)OCCOCCOCCOCCN

Methyltetrazine-PEG4-amine is a PEG-based, amine-functionalized linker designed to connect a methyltetrazine warhead to PROTAC targeting modules. Its polyethylene glycol segment supports aqueous solubility and flexible spacing, while the terminal amine enables robust conjugation to ligands and handles for subsequent assembly. In PROTAC technology, such linkers facilitate modular synthesis and controlled presentation of reactive groups, enabling efficient construction of targeted protein degraders. Detailed structural and reactivity considerations are provided below.

Structure: The linker contains a methyltetrazine moiety connected through a polyethylene glycol chain to a primary amine. It features heteroaromatic ring nitrogen atoms, ether linkages within the PEG backbone, and a terminal nucleophilic amine. These elements collectively provide polarity, conformational flexibility, and compatibility with bioconjugation chemistry.

Reactivity: The methyltetrazine group is suited for bioorthogonal tetrazine–dienophile ligation under mild conditions, enabling rapid attachment of a complementary partner used in PROTAC assembly. The terminal amine can be used for standard amide or urea-forming coupling strategies with activated carboxylic acids or isocyanates, typically employing common coupling reagents and aqueous/organic solvent mixtures. Reaction design should consider tetrazine stability and minimize strongly nucleophilic or highly basic media.

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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

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g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
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