Site-selective installation of an electrophilic handle on proteins for bioconjugation

Site-selective installation of an electrophilic handle on proteins for bioconjugation Bioorganic & Medicinal Chemistry 26 (2018) 3060–3064 Contents lists available at ScienceDirect Bioorganic & Medicinal Chemistry journal homepage: www.elsevier.com/locate/bmc Site-selective installation of an electrophilic handle on proteins for bioconjugation a,d a,d a b a,c,⇑ Bernadette Lee , Shuang Sun , Ester Jiménez-Moreno , André A. Neves , Gonçalo J.L. Bernardes Department of Chemistry, University of Cambridge, Lensfield Road, CB2 1EW Cambridge, UK Li Ka Shing Centre, Cancer Research UK Cambridge Institute, Robinson Way, CB2 0RE Cambridge, UK Instituto de Medicina Molecular, Faculdade de Medicina, Universidade de Lisboa, Avenida Professor Egas Moniz, 1649-028 Lisboa, Portugal ar ti c l e i nf o ab stra ct Article history: Site-selective protein modification strategies can be used to insert non-natural functional groups into Received 16 January 2018 protein structures. Herein, we report on the use of the bis-electrophile 3-bromo-2-bromomethyl-1-pro- Revised 14 February 2018 pene as a reagent to introduce an electrophilic handle at cysteine residues under mild conditions. This Accepted 16 February 2018 method is demonstrated on a variety of proteins containing a solvent-exposed cysteine residue, including Available online 17 February 2018 an anti-HER2 nanobody. Chemically distinct protein conjugates are then efficiently formed through fur- ther reaction of the electrophilic site with http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Bioorganic & Medicinal Chemistry Elsevier

Site-selective installation of an electrophilic handle on proteins for bioconjugation

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Publisher
Elsevier
Copyright
Copyright © 2018 Elsevier Ltd
ISSN
0968-0896
D.O.I.
10.1016/j.bmc.2018.02.028
Publisher site
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Abstract

Bioorganic & Medicinal Chemistry 26 (2018) 3060–3064 Contents lists available at ScienceDirect Bioorganic & Medicinal Chemistry journal homepage: www.elsevier.com/locate/bmc Site-selective installation of an electrophilic handle on proteins for bioconjugation a,d a,d a b a,c,⇑ Bernadette Lee , Shuang Sun , Ester Jiménez-Moreno , André A. Neves , Gonçalo J.L. Bernardes Department of Chemistry, University of Cambridge, Lensfield Road, CB2 1EW Cambridge, UK Li Ka Shing Centre, Cancer Research UK Cambridge Institute, Robinson Way, CB2 0RE Cambridge, UK Instituto de Medicina Molecular, Faculdade de Medicina, Universidade de Lisboa, Avenida Professor Egas Moniz, 1649-028 Lisboa, Portugal ar ti c l e i nf o ab stra ct Article history: Site-selective protein modification strategies can be used to insert non-natural functional groups into Received 16 January 2018 protein structures. Herein, we report on the use of the bis-electrophile 3-bromo-2-bromomethyl-1-pro- Revised 14 February 2018 pene as a reagent to introduce an electrophilic handle at cysteine residues under mild conditions. This Accepted 16 February 2018 method is demonstrated on a variety of proteins containing a solvent-exposed cysteine residue, including Available online 17 February 2018 an anti-HER2 nanobody. Chemically distinct protein conjugates are then efficiently formed through fur- ther reaction of the electrophilic site with

Journal

Bioorganic & Medicinal ChemistryElsevier

Published: Jul 15, 2018

References

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