Peptide/protein stapling and unstapling: introduction of s-tetrazine, photochemical release, and regeneration of the peptide/protein

Journal of the American Chemical Society
Stephen P Brown, Amos B Smith

Abstract

Protocols have been achieved that permit facile introduction of s-tetrazine into unprotected peptides and the protein, thioredoxin, between two cysteine sulfhydryl groups (i.e., staple), followed by photochemical release (i.e., unstaple) and regeneration of the peptide/protein upon removal of the cyano groups from the derived bisthiocyanate. The S,S-tetrazine macrocycles in turn provide a convenient handle for probe introduction by exploiting the inverse electron demand Diels-Alder reactivity of the tetrazine.

References

Jun 1, 1978·Proceedings of the National Academy of Sciences of the United States of America·D F VeberR Hirschmann
Nov 18, 1970·Journal of the American Chemical Society·Y DeganiA Patchornik
Jul 2, 1981·Nature·D F VeberR Hirschmann
Nov 4, 1994·Science·P E DawsonS B Kent
Jul 13, 2000·Proceedings of the National Academy of Sciences of the United States of America·M C AsplundR M Hochstrasser
May 1, 1959·Archives of Biochemistry and Biophysics·G L ELLMAN
Sep 19, 2008·Journal of the American Chemical Society·Melissa L BlackmanJoseph M Fox
Jan 23, 2010·Journal of the American Chemical Society·Mark E B SmithJames R Baker
Apr 15, 2010·Angewandte Chemie·Matthew J TuckerRobin M Hochstrasser
Jun 4, 2011·Nature Protocols·Young-Woo KimGregory L Verdine
Jun 24, 2011·Nature Chemistry·Christopher J White, Andrei K Yudin
May 12, 2012·Journal of Photochemistry and Photobiology. A, Chemistry·Matthew J TuckerRobin M Hochstrasser
Jan 9, 2013·Journal of Nuclear Medicine : Official Publication, Society of Nuclear Medicine·Zhanhong WuFouad Kandeel
Apr 9, 2013·Journal of the American Chemical Society·Alexander M SpokoynyBradley L Pentelute
Aug 28, 2013·Current Opinion in Chemical Biology·Ramajeyam Selvaraj, Joseph M Fox
Oct 10, 2013·Proceedings of the National Academy of Sciences of the United States of America·Matthew J TuckerRobin M Hochstrasser
Jan 10, 2014·Journal of Peptide Science : an Official Publication of the European Peptide Society·Conor M Haney, W Seth Horne
Jan 23, 2014·Chemical Reviews·Miriam Góngora-BenítezFernando Albericio
Feb 15, 2014·Current Medicinal Chemistry·Q Z ZhangZ-G Li
Mar 8, 2014·Journal of Medicinal Chemistry·Loren D Walensky, Gregory H Bird
May 16, 2014·Angewandte Chemie·Aline D de AraujoDavid P Fairlie
Sep 10, 2014·Chemical Society Reviews·Yu Heng LauDavid R Spring

❮ Previous
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Citations

Mar 8, 2016·Macromolecules·Maltish M LorenzoHeather D Maynard
Jan 28, 2016·Science·Ryan GianatassioPhil S Baran
Mar 8, 2016·Organic Letters·Alexander A VinogradovBradley L Pentelute
Mar 2, 2016·ACS Chemical Biology·Philippe DiderichChristian Heinis
Apr 15, 2016·Journal of the American Chemical Society·Xi ChenMyongsoo Lee
May 12, 2016·Biophysical Journal·Rachel M Abaskharon, Feng Gai
Jun 23, 2016·Journal of the American Chemical Society·Guillaume LautretteBradley L Pentelute
Sep 10, 2016·Organic Letters·Omar BrunAnna Grandas
Mar 23, 2017·Journal of the American Chemical Society·Lara R MalinsPhil S Baran
Apr 14, 2017·Journal of the American Chemical Society·Yingqian ZhangChuanzheng Zhou
Mar 28, 2017·Chemistry : a European Journal·Yuanxiang WangDanny Hung-Chieh Chou
Apr 27, 2017·Bioconjugate Chemistry·Kuan HuZigang Li
May 15, 2016·Biopolymers·David P Fairlie, Aline Dantas de Araujo
Jul 1, 2017·Chemical Society Reviews·B L OliveiraG J L Bernardes
Feb 20, 2018·Chemistry : a European Journal·Kenji Watanabe, Takashi Ohshima
Jan 31, 2018·Protein Science : a Publication of the Protein Society·David D BoehrKathleen F O'Rourke
Feb 23, 2018·Angewandte Chemie·Ahmed M EmbabyFrederik Diness
Feb 27, 2018·Chemical Society Reviews·Christopher D SpicerMolly M Stevens
Dec 15, 2015·Chemical Society Reviews·Thomas CastanheiroMihaela Gulea
May 22, 2018·Chemical Communications : Chem Comm·Duo ZhangCarsten Bolm
Jul 28, 2017·Chemistry : a European Journal·Alessandro GoriSilvia Rinaldi
Jun 16, 2018·Angewandte Chemie·Coline CanovasVictor Goncalves
Oct 12, 2018·Medicinal Research Reviews·Kornelia J SkowronTerry W Moore
Sep 27, 2018·Chemistry : a European Journal·Sanne J M VerhoorkChristopher R Coxon
Nov 10, 2018·Chemistry : a European Journal·Manuel G RicardoLudger A Wessjohann
Dec 27, 2018·Journal of Peptide Science : an Official Publication of the European Peptide Society·Mareen Pagel
Nov 7, 2018·Angewandte Chemie·Chi ZhangBradley L Pentelute
Feb 16, 2019·Chemical Communications : Chem Comm·Kengo HanayaZachary T Ball
Jun 19, 2019·Angewandte Chemie·Mihajlo TodorovicDavid M Perrin
Jul 23, 2019·Chemical Communications : Chem Comm·Naomi S RobertsonDavid R Spring
Sep 21, 2019·Angewandte Chemie·Sadasivam JeganathanTom N Grossmann
Jan 1, 2016·Chemical Science·Maximillian T W LeeVijay Chudasama
Jul 13, 2018·Chemical Science·Philippe BisseretNicolas Blanchard
Jun 17, 2020·Organic & Biomolecular Chemistry·Neelesh C ReddyVishal Rai
Oct 4, 2017·Chemical Science·Claire M GrisonAndrew J Wilson
Feb 20, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Aldrin V VascoLudger A Wessjohann
Nov 7, 2017·Chembiochem : a European Journal of Chemical Biology·Shuang SunGonçalo J L Bernardes
Jun 1, 2016·Chemical Science·S Kalhor-MonfaredR Derda
Oct 6, 2020·Research : a Science Partner Journal·Changping WangYiyun Cheng
Aug 31, 2016·Topics in Current Chemistry·Haoxing Wu, Neal K Devaraj
Jul 21, 2015·Angewandte Chemie·Yuanxiang Wang, Danny Hung-Chieh Chou
Jan 21, 2016·Chembiochem : a European Journal of Chemical Biology·Annemieke Madder, Smita B Gunnoo

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Methods Mentioned

BETA
peptide folding
reverse-phase chromatography

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