A Minimal, Unstrained S-Allyl Handle for Pre-Targeting Diels-Alder Bioorthogonal Labeling in Live Cells


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Authors
Oliveira, BL 
Guo, Z 
Boutureira, O 
Guerreiro, A 
Jiménez-Osés, G 
Abstract

The unstrained S-allyl cysteine amino acid was site-specifically installed on apoptosis protein biomarkers and was further used as a chemical handle and ligation partner for 1,2,4,5-tetrazines by means of an inverse-electron-demand Diels-Alder reaction. We demonstrate the utility of this minimal handle for the efficient labeling of apoptotic cells using a fluorogenic tetrazine dye in a pre-targeting approach. The small size, easy chemical installation, and selective reactivity of the S-allyl handle towards tetrazines should be readily extendable to other proteins and biomolecules, which could facilitate their labeling within live cells.

Description
Keywords
apoptosis, bioorthogonal labeling, Diels-Alder reactions, pre-targeting, unstrained alkenes
Journal Title
Angewandte Chemie International Edition
Conference Name
Journal ISSN
1433-7851
1521-3773
Volume Title
55
Publisher
Wiley
Sponsorship
Engineering and Physical Sciences Research Council (EP/M003647/1)
European Research Council (676832)
European Commission Horizon 2020 (H2020) Marie Sk?odowska-Curie actions (702574)
European Commission (EC) (852985)
China Scholarship Council, FCT Portugal, European Union (Marie-Sklodowska Curie ITN Protein Conjugates; Marie-Sklodowska Curie IEF), MINECO (CTQ2015-70524-R and RYC-2013-14706), Engineering and Physical Sciences Research Council, BiFi (Memento cluster), Royal Society, European Research Council