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
Bioorganic & Medicinal Chemistry – Elsevier
Published: Jul 15, 2018
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