Palladium-Catalyzed Chemoselective and Biocompatible Functionalization of Cysteine-Containing Molecules at Room Temperature

Riyadh Ahmed Atto Al-Shuaeeb; Sergii Kolodych; Oleksandr Koniev; Sébastien Delacroix; Stéphane Erb; Stéphanie Nicolaÿ; Jean Christophe Cintrat; Jean Daniel Brion; Sarah Cianférani; Mouâd Alami; Alain Wagner; Samir Messaoudi

doi:10.1002/chem.201602277

Palladium-Catalyzed Chemoselective and Biocompatible Functionalization of Cysteine-Containing Molecules at Room Temperature

Riyadh Ahmed Atto Al-Shuaeeb, Sergii Kolodych, Oleksandr Koniev, Sébastien Delacroix, Stéphane Erb, Stéphanie Nicolaÿ, Jean Christophe Cintrat, Jean Daniel Brion, Sarah Cianférani, Mouâd Alami, Alain Wagner, Samir Messaoudi

Research output: Contribution to journal › Article › peer-review

Abstract

The third generation of aminobiphenyl palladacycle pre-catalyst “G3-Xantphos” enables functionalization of peptides containing cysteine in high yields. The conjugation (bioconjugation) occurs chemoselectively at room temperature under biocompatible conditions. Extension of the method to protein functionalization allows selective bioconjugation of the trastuzumab antibody.

Original language	English
Pages (from-to)	11365-11370
Number of pages	6
Journal	Chemistry - A European Journal
Volume	22
Issue number	32
DOIs	https://doi.org/10.1002/chem.201602277
Publication status	Published - 1 Aug 2016
Externally published	Yes

Keywords

C−S bond-forming reaction
amino acids
antibody–drug conjugates
bioconjugation
palladium catalysis
peptides

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10.1002/chem.201602277

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Al-Shuaeeb, R. A. A., Kolodych, S., Koniev, O., Delacroix, S., Erb, S., Nicolaÿ, S., Cintrat, J. C., Brion, J. D., Cianférani, S., Alami, M., Wagner, A., & Messaoudi, S. (2016). Palladium-Catalyzed Chemoselective and Biocompatible Functionalization of Cysteine-Containing Molecules at Room Temperature. Chemistry - A European Journal, 22(32), 11365-11370. https://doi.org/10.1002/chem.201602277

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title = "Palladium-Catalyzed Chemoselective and Biocompatible Functionalization of Cysteine-Containing Molecules at Room Temperature",

abstract = "The third generation of aminobiphenyl palladacycle pre-catalyst “G3-Xantphos” enables functionalization of peptides containing cysteine in high yields. The conjugation (bioconjugation) occurs chemoselectively at room temperature under biocompatible conditions. Extension of the method to protein functionalization allows selective bioconjugation of the trastuzumab antibody.",

keywords = "C−S bond-forming reaction, amino acids, antibody–drug conjugates, bioconjugation, palladium catalysis, peptides",

author = "Al-Shuaeeb, \{Riyadh Ahmed Atto\} and Sergii Kolodych and Oleksandr Koniev and S{\'e}bastien Delacroix and St{\'e}phane Erb and St{\'e}phanie Nicola{\"y} and Cintrat, \{Jean Christophe\} and Brion, \{Jean Daniel\} and Sarah Cianf{\'e}rani and Mou{\^a}d Alami and Alain Wagner and Samir Messaoudi",

note = "Publisher Copyright: {\textcopyright} 2016 WILEY-VCH Verlag GmbH \& Co. KGaA, Weinheim",

year = "2016",

month = aug,

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doi = "10.1002/chem.201602277",

language = "English",

volume = "22",

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journal = "Chemistry - A European Journal",

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Al-Shuaeeb, RAA, Kolodych, S, Koniev, O, Delacroix, S, Erb, S, Nicolaÿ, S, Cintrat, JC, Brion, JD, Cianférani, S, Alami, M, Wagner, A & Messaoudi, S 2016, 'Palladium-Catalyzed Chemoselective and Biocompatible Functionalization of Cysteine-Containing Molecules at Room Temperature', Chemistry - A European Journal, vol. 22, no. 32, pp. 11365-11370. https://doi.org/10.1002/chem.201602277

TY - JOUR

T1 - Palladium-Catalyzed Chemoselective and Biocompatible Functionalization of Cysteine-Containing Molecules at Room Temperature

AU - Al-Shuaeeb, Riyadh Ahmed Atto

AU - Kolodych, Sergii

AU - Koniev, Oleksandr

AU - Delacroix, Sébastien

AU - Erb, Stéphane

AU - Nicolaÿ, Stéphanie

AU - Cintrat, Jean Christophe

AU - Brion, Jean Daniel

AU - Cianférani, Sarah

AU - Alami, Mouâd

AU - Wagner, Alain

AU - Messaoudi, Samir

PY - 2016/8/1

Y1 - 2016/8/1

N2 - The third generation of aminobiphenyl palladacycle pre-catalyst “G3-Xantphos” enables functionalization of peptides containing cysteine in high yields. The conjugation (bioconjugation) occurs chemoselectively at room temperature under biocompatible conditions. Extension of the method to protein functionalization allows selective bioconjugation of the trastuzumab antibody.

AB - The third generation of aminobiphenyl palladacycle pre-catalyst “G3-Xantphos” enables functionalization of peptides containing cysteine in high yields. The conjugation (bioconjugation) occurs chemoselectively at room temperature under biocompatible conditions. Extension of the method to protein functionalization allows selective bioconjugation of the trastuzumab antibody.

KW - C−S bond-forming reaction

KW - amino acids

KW - antibody–drug conjugates

KW - bioconjugation

KW - palladium catalysis

KW - peptides

U2 - 10.1002/chem.201602277

DO - 10.1002/chem.201602277

M3 - Article

C2 - 27362372

AN - SCOPUS:84976902582

SN - 0947-6539

VL - 22

SP - 11365

EP - 11370

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

IS - 32

ER -

Palladium-Catalyzed Chemoselective and Biocompatible Functionalization of Cysteine-Containing Molecules at Room Temperature

Abstract

Keywords

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