On the bioactive conformation of the rhodopsin chromophore: Absolute sense of twist around the 6-s-cis bond

Yukari Fujimoto; Jun Ishihara; Shojiro Maki; Naoko Fujioka; Tao Wang; Takumi Furuta; Nathan Fishkin; Babak Borhan; Nina Berova; Koji Nakanishi

doi:10.1002/1521-3765(20011001)7:19<4198::AID-CHEM4198>3.0.CO;2-X

On the bioactive conformation of the rhodopsin chromophore: Absolute sense of twist around the 6-s-cis bond

Yukari Fujimoto, Jun Ishihara, Shojiro Maki, Naoko Fujioka, Tao Wang, Takumi Furuta, Nathan Fishkin, Babak Borhan, Nina Berova, Koji Nakanishi

Research output: Contribution to journal › Article

41 Citations (Scopus)

Abstract

Incubation of opsin with synthetic 6-s-locked retinoids 2a and 2b only led to pigment formation from the alpha-locked 2a, the CD spectrum of which was similar to that of native rhodopsin (Rh). This establishes that the 6-s-bond of the chromophore in rhodopsin is cis, and that its helicity is negative. Earlier cross-linking studies showed that the 11-cis to all-trans photoisomerization occurring in the batho-Rh to lumi-Rh conversion induces a flip over of the side carrying the ring moiety. The GTP-binding assay of pigment Rh-(2a), incorporating retinal analogue 2a, has shown that its activity is 80% that of the native pigment. That is, the overall conformation around the 6-s bond is retained in the steps leading to G-protein activation.

Original language	English
Pages (from-to)	4198-4204
Number of pages	7
Journal	Chemistry - A European Journal
Volume	7
Issue number	19
DOIs	https://doi.org/10.1002/1521-3765(20011001)7:19<4198::AID-CHEM4198>3.0.CO;2-X
Publication status	Published - 2001 Oct 1
Externally published	Yes

Keywords

Chirality
Circular dichroism
Conformation analysis
Receptors
Retinal
Rhodopsin

ASJC Scopus subject areas

Catalysis
Organic Chemistry

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10.1002/1521-3765(20011001)7:19<4198::AID-CHEM4198>3.0.CO;2-X

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Fujimoto, Y., Ishihara, J., Maki, S., Fujioka, N., Wang, T., Furuta, T., Fishkin, N., Borhan, B., Berova, N., & Nakanishi, K. (2001). On the bioactive conformation of the rhodopsin chromophore: Absolute sense of twist around the 6-s-cis bond. Chemistry - A European Journal, 7(19), 4198-4204. https://doi.org/10.1002/1521-3765(20011001)7:19<4198::AID-CHEM4198>3.0.CO;2-X

On the bioactive conformation of the rhodopsin chromophore : Absolute sense of twist around the 6-s-cis bond. / Fujimoto, Yukari; Ishihara, Jun; Maki, Shojiro; Fujioka, Naoko; Wang, Tao; Furuta, Takumi; Fishkin, Nathan; Borhan, Babak; Berova, Nina; Nakanishi, Koji.

In: Chemistry - A European Journal, Vol. 7, No. 19, 01.10.2001, p. 4198-4204.

Research output: Contribution to journal › Article

Fujimoto, Y, Ishihara, J, Maki, S, Fujioka, N, Wang, T, Furuta, T, Fishkin, N, Borhan, B, Berova, N & Nakanishi, K 2001, 'On the bioactive conformation of the rhodopsin chromophore: Absolute sense of twist around the 6-s-cis bond', Chemistry - A European Journal, vol. 7, no. 19, pp. 4198-4204. https://doi.org/10.1002/1521-3765(20011001)7:19<4198::AID-CHEM4198>3.0.CO;2-X

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