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Literature DB >> 27362372

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

Riyadh Ahmed Atto Al-Shuaeeb¹, Sergii Kolodych², Oleksandr Koniev², Sébastien Delacroix², Stéphane Erb^3,4, Stéphanie Nicolaÿ⁵, Jean-Christophe Cintrat⁶, Jean-Daniel Brion¹, Sarah Cianférani^3,4, Mouâd Alami¹, Alain Wagner⁷, Samir Messaoudi⁸.

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.

Entities: Chemical

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

Mesh：

Substances：

Year: 2016 PMID： 27362372 DOI： 10.1002/chem.201602277

Source DB: PubMed Journal: Chemistry ISSN： 0947-6539 Impact factor: 5.236

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Cited

6 in total

Review 1. Arylation Chemistry for Bioconjugation.

Authors: Chi Zhang; Ekaterina V Vinogradova; Alexander M Spokoyny; Stephen L Buchwald; Bradley L Pentelute
Journal: Angew Chem Int Ed Engl Date: 2019-02-15 Impact factor: 15.336

Review 2. Residue-Specific Peptide Modification: A Chemist's Guide.

Authors: Justine N deGruyter; Lara R Malins; Phil S Baran
Journal: Biochemistry Date: 2017-07-17 Impact factor: 3.162

3. Cyclometalated Au^III Complexes for Cysteine Arylation in Zinc Finger Protein Domains: towards Controlled Reductive Elimination.

Authors: Margot N Wenzel; Riccardo Bonsignore; Sophie R Thomas; Didier Bourissou; Giampaolo Barone; Angela Casini
Journal: Chemistry Date: 2019-05-09 Impact factor: 5.236

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

Review 1. Arylation Chemistry for Bioconjugation.

Review 2. Residue-Specific Peptide Modification: A Chemist's Guide.

3. Cyclometalated Au^III Complexes for Cysteine Arylation in Zinc Finger Protein Domains: towards Controlled Reductive Elimination.

4. Pd(II)-Mediated C-H Activation for Cysteine Bioconjugation.

5. An Organometallic Strategy for Cysteine Borylation.

Review 6. Aryl transition metal chemical warheads for protein bioconjugation.

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

Review 1. Arylation Chemistry for Bioconjugation.

Review 2. Residue-Specific Peptide Modification: A Chemist's Guide.

3. Cyclometalated AuIII Complexes for Cysteine Arylation in Zinc Finger Protein Domains: towards Controlled Reductive Elimination.

4. Pd(II)-Mediated C-H Activation for Cysteine Bioconjugation.

5. An Organometallic Strategy for Cysteine Borylation.

Review 6. Aryl transition metal chemical warheads for protein bioconjugation.

3. Cyclometalated Au^III Complexes for Cysteine Arylation in Zinc Finger Protein Domains: towards Controlled Reductive Elimination.