MAPN: First-in-Class Reagent for Kinetically Resolved Thiol-to-Thiol Conjugation

Bioconjugate Chemistry
Oleksandr KonievAlain Wagner

Abstract

Thiols are among the most frequently used functional groups in the field of bioconjugation. While there exists a variety of heterobifunctional reagents that allow for coupling thiols to other functions (e.g., amines, carboxylic acids), there is no specific reagent for creating heteroconjugates using two different thiols. In response to the ever-increasing demand for bioconjugation tools, we have developed p-(maleimide)-phenylpropionitrile (MAPN)-an efficient reagent for kinetically resolved thiol-to-thiol coupling. In a comparative study with its closest commercially available analogue, p-phenylenedimaleimide, MAPN has shown substantial advantages for the preparation of thiol-thiol heteroconjugates. Namely, an antibody-drug conjugate (ADC) with mertansine (DM1), conjugated to the cysteine residues of Trastuzumab, was prepared for the first time.

References

Nov 16, 2007·Organic & Biomolecular Chemistry·Frank Brotzel, Herbert Mayr
Feb 25, 2009·Chemistry, an Asian Journal·Justin M ChalkerBenjamin G Davis
Jan 15, 2014·Bioconjugate Chemistry·Oleksandr KonievAlain Wagner

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Citations

Mar 7, 2017·Chemistry : a European Journal·Omar BoutureiraGonçalo J L Bernardes
Jul 1, 2016·Chemistry : a European Journal·Riyadh Ahmed Atto Al-ShuaeebSamir Messaoudi
Oct 28, 2017·Organic & Biomolecular Chemistry·Elisabetta TobaldiAlain Wagner
Jan 2, 2020·Chemical Science·Igor DovganAlain Wagner

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