2,5-Dioxo-1-pyrrolidinyl 5-[4-(1,2,4,5-tetrazin-3-yl)benzylamino]-5-oxopentanoate

 CAS No.: 1244040-64-9  Cat No.: BP-501706 4.5  

2,5-Dioxo-1-pyrrolidinyl 5-[4-(1,2,4,5-tetrazin-3-yl)benzylamino]-5-oxopentanoate is a bifunctional PROTAC linker–like intermediate featuring a succinimide (pyrrolidinyl dione) handle connected through a glutarate-type spacer to a benzylamino-substituted tetrazine aromatic motif. The succinimide ester functionality is well suited for chemoselective conjugation to primary amines on ligands or targeting modules, enabling stable amide bond formation under standard bioconjugation conditions. The extended amino acid–like chain provides conformational flexibility to tune the relative orientation of the conjugated components, which is critical for productive ternary complex formation in targeted protein degradation workflows. The tetrazine group serves as a bioorthogonal reactive moiety for inverse-electron-demand Diels–Alder ligation, allowing rapid attachment or exchange of partner fragments in modular PROTAC assembly strategies. This compound is valuable for researchers seeking efficient, stepwise construction of degraders and for optimizing linker length and geometry to improve degradation potency and selectivity.

2,5-Dioxo-1-pyrrolidinyl 5-[4-(1,2,4,5-tetrazin-3-yl)benzylamino]-5-oxopentanoate

Structure of 1244040-64-9

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PROTAC Linker
Molecular Formula
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Molecular Weight
398.37

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IUPACName
(2,5-dioxopyrrolidin-1-yl) 5-oxo-5-[[4-(1,2,4,5-tetrazin-3-yl)phenyl]methylamino]pentanoate
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This tetrazine-bearing NHS ester is a dual-reactive linker for amine labeling and bioorthogonal conjugation. Its activated ester enables covalent attachment to amine-containing ligands, while the tetrazine unit supports rapid IEDDA ligation with strained alkene partners. The molecule is described in detail below.

Structure: The molecule contains a 1,2,4,5-tetrazine-substituted benzyl amide connected to a glutarate-derived N-hydroxysuccinimide ester. The aromatic tetrazine segment provides bioorthogonal reactivity, while the succinimidyl ester serves as an amine-reactive acylating group for linker installation.

Reactivity: The NHS ester reacts with primary amines under mildly basic, anhydrous or buffered conditions to form stable amide bonds. The tetrazine moiety then undergoes inverse-electron-demand Diels-Alder ligation with strained alkene partners such as TCO. Avoid nucleophilic buffers during ester coupling, and protect the tetrazine from strong reductants or prolonged harsh conditions.

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It is commonly abbreviated as: C1V1 = C2V2

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Tip: Chemical formula is case sensitive. C22H30N4O c22h30n40
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