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

Terrence Kantner; Bayan Alkhawaja; Andrew Watts

doi:10.1021/acsomega.7b01094

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

Terrence Kantner, Bayan Alkhawaja, Andrew Watts

Department of Life Sciences

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5 Citations (SciVal)

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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.

Original language	English
Pages (from-to)	5785-5791
Number of pages	7
Journal	ACS OMEGA
Volume	2
Issue number	9
Early online date	14 Sep 2017
DOIs	https://doi.org/10.1021/acsomega.7b01094
Publication status	Published - 30 Sep 2017

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10.1021/acsomega.7b01094Licence: CC BY

Kantner-ACS OMEGAFinal published version, 1.29 MBLicence: CC BY

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title = "In Situ Quenching of Trialkylphosphine Reducing Agents Using Water-Soluble PEG-Azides Improves Maleimide Conjugation to Proteins",

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.",

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Y1 - 2017/9/30

N2 - 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.

AB - 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.

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U2 - 10.1021/acsomega.7b01094

DO - 10.1021/acsomega.7b01094

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SN - 2470-1343

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

Abstract

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Enhanced Oral Delivery of Biopharmaceuticals

Andrew Watts

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

Abstract

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