The E1 mechanism in photo-induced beta-elimination reactions for green-to-red conversion of fluorescent proteins

Chemistry & Biology
Hidekazu TsutsuiAtsushi Miyawaki

Abstract

KikGR is a fluorescent protein engineered to display green-to-red photoconvertibility that is induced by irradiation with ultraviolet or violet light. Similar to Kaede and EosFP, two naturally occurring photoconvertible proteins, KikGR contains a His(62)-Tyr(63)-Gly(64) tripeptide sequence, which forms a green chromophore that can be photoconverted to a red one via formal beta-elimination and subsequent extension of a pi-conjugated system. Using a crystallizable variant of KikGR, we determined the structures of both the green and red state at 1.55 A resolution. The double bond between His(62)-C(alpha) and His(62)-C(beta) in the red chromophore is in a cis configuration, indicating that rotation along the His(62) C(alpha)-C(beta) bond occurs following cleavage of the His(62) N(alpha)-C(alpha) bond. This structural rearrangement provides evidence that the beta-elimination reaction governing the green-to-red photoconversion of KikGR follows an E1 (elimination, unimolecular) mechanism.

References

Oct 1, 1996·Nature Biotechnology·F YangG N Phillips
Oct 3, 1998·Acta Crystallographica. Section D, Biological Crystallography·A T BrüngerG L Warren
Oct 6, 1998·Annual Review of Biochemistry·R Y Tsien
Apr 4, 2002·Proceedings of the National Academy of Sciences of the United States of America·Y A LabasM V Matz
Sep 14, 2002·Science·George H Patterson, Jennifer Lippincott-Schwartz
Sep 25, 2002·Proceedings of the National Academy of Sciences of the United States of America·Ryoko AndoAtsushi Miyawaki
Oct 29, 2003·Molecular Cell·Hideaki MizunoAtsushi Miyawaki
Oct 27, 2004·Proceedings of the National Academy of Sciences of the United States of America·Jörg WiedenmannG Ulrich Nienhaus
Feb 26, 2005·EMBO Reports·Hidekazu TsutsuiAtsushi Miyawaki
Jun 21, 2005·Proceedings of the National Academy of Sciences of the United States of America·Karin NienhausHerbert Nar
Aug 10, 2006·Nature Methods·Michael J RustXiaowei Zhuang
Aug 12, 2006·Science·Eric BetzigHarald F Hess
Sep 19, 2006·Biophysical Journal·Samuel T HessMichael D Mason
Oct 25, 2007·Journal of the American Chemical Society·Cristina FlorsJohan Hofkens
Jun 25, 2008·Proceedings of the National Academy of Sciences of the United States of America·Hideaki MizunoAtsushi Miyawaki

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Citations

May 9, 2012·Chemical Reviews·Fedor V Subach, Vladislav V Verkhusha
Apr 1, 2016·Scientific Reports·Sheldon J J KwokSeok-Hyun Yun
May 24, 2012·Biochemical Society Transactions·Dominique BourgeoisVirgile Adam
Jun 3, 2017·International Journal of Molecular Sciences·Dominique Bourgeois
Mar 17, 2015·Molecular Cell·Hidekazu TsutsuiAtsushi Miyawaki
Sep 24, 2013·Chemical Society Reviews·Karin Nienhaus, G Ulrich Nienhaus
Dec 25, 2013·Photochemical & Photobiological Sciences : Official Journal of the European Photochemistry Association and the European Society for Photobiology·Eduard FronHideaki Mizuno
Aug 18, 2017·International Journal of Molecular Sciences·Rebekka M Wachter
Sep 11, 2020·International Journal of Molecular Sciences·Xiaocen LuRobert E Campbell
Aug 5, 2016·Acta Crystallographica. Section D, Structural Biology·Nadya V PletnevaVladimir Z Pletnev
Sep 9, 2016·Journal of Physics. Condensed Matter : an Institute of Physics Journal·Karin Nienhaus, G Ulrich Nienhaus
Jul 20, 2018·Frontiers in Immunology·Akira NguyenTri Giang Phan
Jul 7, 2010·Journal of Molecular Biology·Hiofan HoiRobert E Campbell
Aug 6, 2021·Chemical Science·Xiaocen LuRobert E Campbell
Jan 30, 2013·The Journal of Physical Chemistry. B·Eduard FronVirgile Adam
Jul 30, 2010·Biochemistry·Rebekka M WachterHanseong Kim
Aug 18, 2020·The Journal of Physical Chemistry. B·Clyde FareJasper J van Thor
Oct 14, 2010·Biochimica Et Biophysica Acta·Stefano BettatiRoberto Battistutta

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