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.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 Counci

Bernardes, GJL

Boutureira, O

Guerreiro, A

Guo, Z

Jiménez-Osés, G

Oliveira, BL

PubMed

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 DielsAlder 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. © 2016 Wiley-VCH Verlag GmbH & Co. KGaA, Weinhei

Oliveira, B.L.

Guo, Z.

Boutureira, O.

Guerreiro, A.

Jiménez-Osés, G.

Bernardes, G.J.L.

Repositorio de Universidad de La Rioja

English

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

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

CUED - Cambridge University Engineering Department

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

Apollo (Cambridge)

Bruno L. Oliveira

Zijian Guo

Omar Boutureira

Ana Guerreiro

Gonzalo Jiménez‐Osés

Gonçalo J. L. Bernardes

Crossref

Angewandte Chemie International Edition

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

5 pags, 3 figsThe 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.We thank China Scholarship Council (PhD studentship to Z.G.), FCT Portugal (FCT Investigator to G.J.L.B.), and the EU (Marie-Sklodowska Curie ITN Protein Conjugates; Marie-Sklodowska Curie IEF to B.L.O. and O.B.), MINECO (CTQ2015-70524-R and RYC-2013-14706 to G.J.O.), and the EPSRC for funding. We also thank Dr. André Neves and Prof. Kevin Brindle for providing the C2Am protein; Beatrice Amgarten for expressing and purifying Annexin V; Dr. Mike Deery and Ms. Julie Howard for help with mass spectrometry analysis; and BiFi (Memento cluster) for computer support. G.J.L.B. is a Royal Society University Research Fellow and the recipient of a European Research Council Starting Grant (TagIt).Peer reviewe

Oliveira, Bruno L.

Guo, Zijian

Boutureira, Omar

Guerreiro, Ana

Jiménez-Osés, Gonzalo

Bernardes, Gonçalo J. L.

Digital.CSIC

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

Repositorio Universidad de Zaragoza

© 2016 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.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.We thank China Scholarship Council (PhD studentship to Z.G.), FCT Portugal (FCT Investigator to G.J.L.B.), and the EU (Marie-Sklodowska Curie ITN Protein Conjugates; Marie-Sklodowska Curie IEF to B.L.O. and O.B.), MINECO (CTQ2015-70524-R and RYC-2013-14706 to G.J.O.), and the EPSRC for funding.info:eu-repo/semantics/publishedVersio

Jiménez‐Osés, Gonzalo

Universidade de Lisboa: Repositório.UL

A minimal, unstrained S‐Allyl handle for pre‐targeting Diels–Alder bioorthogonal labeling in live cells

The unstrained S-allyl cysteine amino acid was sitespecifically 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

http://zaguan.unizar.es/record/57789/files/texto_completo.pdf

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

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Repositorio de Universidad de La Rioja

CUED - Cambridge University Engineering Department

Apollo (Cambridge)

Crossref

Digital.CSIC

Repositorio Universidad de Zaragoza

Universidade de Lisboa: Repositório.UL

CUED - Cambridge University Engineering Department