Barrierless Photoisomerization of 11-cis Retinal Protonated Schiff Base in Solution | Zendy

Giovanni Bassolino | Zendy; Tina Sovdat | Zendy; Alex Soares Duarte | Zendy; Jong Min Lim | Zendy; Christoph Schnedermann | Zendy; Matz Liebel | Zendy; Barbara Odell | Zendy; Timothy D. W. Claridge | Zendy; Stephen P. Fletcher | Zendy; Philipp Kukura | Zendy

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Barrierless Photoisomerization of 11-cis Retinal Protonated Schiff Base in Solution

Author(s) -

Giovanni Bassolino,

Tina Sovdat,

Alex Soares Duarte,

Jong Min Lim,

Christoph Schnedermann,

Matz Liebel,

Barbara Odell,

Timothy D. W. Claridge,

Stephen P. Fletcher,

Philipp Kukura

Publication year - 2015

Publication title -

journal of the american chemical society

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 7.115

H-Index - 612

eISSN - 1520-5126

pISSN - 0002-7863

DOI - 10.1021/jacs.5b06492

Subject(s) - photoisomerization , chemistry , chromophore , protonation , schiff base , rhodopsin , photochemistry , retinal , isomerization , stereochemistry , organic chemistry , catalysis , ion , biochemistry

A hallmark of the primary visual event is the barrierless, ultrafast, and efficient 11-cis to all-trans photoisomerization of the retinal protonated Schiff base (RPSB) chromophore. The remarkable reactivity of RPSB in the visual pigment rhodopsin has been attributed to potential energy surface modifications enabled by evolution-optimized chromophore-protein interactions. Here, we use a combined synthetic and ultrafast spectroscopic approach to show that barrierless photoisomerization is an intrinsic property of 11-cis RPSB, suggesting that the protein may merely adjust the ratio between fast reactive and slow unreactive decay channels. These results call for a re-evaluation of our understanding and theoretical description of RPSB photochemistry.

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