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

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Keywords

Chirality
Circular dichroism
Conformation analysis
Receptors
Retinal
Rhodopsin

ASJC Scopus subject areas

Catalysis
Organic Chemistry

Cite this

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