TCO-PNB ester
CAS No.: 1438415-89-4
Cat No.: BP-501619
Purity: 95%
4.5 
TCO-PNB ester is a strained trans-cyclooctene (TCO)–bearing activated ester derived from p-nitrophenyl (PNB) carbonate/ester chemistry, designed for efficient, bioorthogonal conjugation in PROTAC-related workflows. Structurally, it provides a cyclooctene “handle” that undergoes rapid inverse-electron-demand Diels–Alder reactivity with tetrazine partners, enabling controllable linkage formation under mild conditions. The PNB ester serves as a robust leaving-group electrophile for acyl transfer, allowing the TCO moiety to be installed onto amine or hydroxyl-containing building blocks (e.g., linker termini or ligands) to generate PROTAC intermediates with defined attachment points. In targeted protein degradation research, this dual functionality supports modular synthesis of degradation constructs and facilitates post-synthetic assembly or labeling strategies that preserve ligand affinity and ternary-complex formation. Its value lies in improving reaction specificity and timing for assembling multi-component degraders, thereby streamlining optimization of linker architecture and conjugation efficiency.
Structure of 1438415-89-4
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TCO-PNB ester is a reactive PROTAC linker building block designed to enable efficient conjugation between targeting ligands and downstream degradation modules. Its activated 4-nitrophenyl carbonate functionality supports amine-reactive linker installation under standard organic synthesis conditions. The molecule’s trans-cyclooctene reactivity profile is particularly useful for controlled bioorthogonal conjugation workflows, and the following sections describe its structural features and practical assembly considerations in detail.
Structure: TCO-PNB ester contains a trans-cyclooctene core bearing an activated 4-nitrophenyl carbonate group. The structure features an alkene within a strained cyclooctene framework and an activated aromatic carbonate, providing a reactive electrophilic center for amine conjugation.
Reactivity: The activated 4-nitrophenyl carbonate reacts with primary amines by nucleophilic substitution to form carbamate linkages, with 4-nitrophenoxide serving as the leaving group. Typical conditions use polar aprotic solvents and mild base to promote nucleophile generation while preserving the trans-cyclooctene functionality. For subsequent bioorthogonal steps, the strained alkene can undergo rapid inverse-electron-demand cycloaddition with tetrazines under aqueous-compatible conditions, often without added catalysts.
* 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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