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Self-Immolative Hydroxybenzylamine Linkers for Traceless Protein Modification.

Douglas A Rose¹, Joseph W Treacy¹, Zhongyue J Yang¹

¹Department of Chemistry and Biochemistry and California NanoSystems Institute, University of California, Los Angeles, 607 Charles E. Young Drive East, Los Angeles, California 90095-1569, United States.

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|March 24, 2022

Summary

Researchers developed new traceless self-immolative linkers based on hydroxybenzylamines. These linkers offer tunable payload release rates for reversible bioconjugation, enhancing protein modification strategies.

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Area of Science:

Organic Chemistry
Bioconjugation Chemistry
Polymer Chemistry

Background:

Traceless self-immolative linkers are crucial for reversible protein and peptide modification.
Existing linkers have limitations in tunability and release kinetics.

Purpose of the Study:

To introduce a new class of hydroxybenzylamine-based traceless linkers.
To modulate linker release rates through electronic modifications.
To demonstrate their utility in reversible bioconjugation.

Main Methods:

Synthesis of a library of hydroxybenzylamine linkers with varied electronic properties.
Kinetic studies to determine linker half-lives (20-144 h).
Density Functional Theory (DFT) for mechanistic insights and *in silico* design.
Preparation and characterization of protein-polymer conjugates.

Main Results:

Linker release rates were successfully modulated by aromatic core substituents, with half-lives ranging from 20 to 144 hours.
DFT calculations guided the design of a faster linker with a 4.6-hour half-life.
Reversible protein-polyethylene glycol conjugates showed significant activity recovery (≥94%) upon polymer release.

Conclusions:

A new class of tunable traceless self-immolative linkers based on hydroxybenzylamines was developed.
These linkers offer controlled payload release for advanced bioconjugation applications.
The developed linkers expand the available tools for reversible modification of biomolecules.