In Situ Quenching of Trialkylphosphine Reducing Agents Using Water-Soluble PEG-Azides Improves Maleimide Conjugation to Proteins.

ACS Omega
Terrence KantnerAndrew G Watts

Abstract

Trialkylphosphines tris(2-carboxy-ethyl)-phosphine and tris(3-hydroxypropyl)-phosphine are popular reagents for the reduction of cysteine residues in bioconjugation reactions using maleimides. However, it has been demonstrated that these phosphines are reactive toward maleimide, necessitating their removal before the addition of the Michael acceptor. Here, a method using water-soluble PEG-azides is reported for the quenching of trialkylphosphines in situ, which is demonstrated to improve the level of maleimide conjugation to proteins.

References

Jul 23, 2003·Electrophoresis·Kamala TyagarajanJohn E Wiktorowicz
Mar 23, 2005·Molecular Immunology·Socorro EspuelasFrancis Schuber
May 23, 2007·Bioorganic & Medicinal Chemistry·Kimberly M BongerGijsbert A van der Marel
Feb 16, 2008·Bioconjugate Chemistry·Younggyu KimShimon Weiss
May 30, 2013·Bioconjugate Chemistry·Katherine CumnockFredric Jacobson
Aug 8, 2014·Bioconjugate Chemistry·James T PattersonCarlos F Barbas
Apr 5, 2016·Proceedings of the National Academy of Sciences of the United States of America·Avital PercherHoward C Hang

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Citations

Mar 21, 2020·Chembiochem : a European Journal of Chemical Biology·Sinenhlanhla N MthembuBeatriz G de la Torre

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Methods Mentioned

BETA
column chromatography
electrophoresis
NMR

Software Mentioned

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