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August 27, 2026Bioconjugate ChemistryOpen Access

Solvatochromism and Click Reactivity of Yellow Tetrazines

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Authors

PKPatrick KeppelJRJakob RafflerHMHannes Mikula

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Overview

Chemical analysis demonstrates pH-dependent solvatochromism and altered Diels-Alder click reactivity in hydroxypyridyl-tetrazines, indicating key design principles for bioorthogonal bond cleavage.

Key Points

  • To identify the structural origin of solvatochromism in hydroxypyridyl-substituted 1,2,4,5-tetrazines and determine how phenolic deprotonation alters bioorthogonal click reactivity.
  • Examined the optical properties and solvatochromic color shifts of hydroxypyridyl-substituted 1,2,4,5-tetrazines in methanol and buffered aqueous solutions.
  • Assessed the protonation states of the phenolic OH group under varying solution conditions.
  • Measured the kinetics of the Diels-Alder cycloaddition reaction across a range of aqueous pH values.
  • Solvatochromic yellow coloration in hydroxypyridyl-tetrazines is driven by the deprotonation of the phenolic hydroxyl group.
  • Reaction rates of the bioorthogonal Diels-Alder cycloaddition shift significantly in response to changes in the pH of the aqueous solution.

Cite This Study

Keppel et al. (2026) studied this question.

synapsesocial.com/papers/6a9bf5ded8d8bde79ebb1436https://doi.org/10.1021/acs.bioconjchem.6c00097
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