Properties of several sterically modified retinal analogs and their photosensitive pigments

Ebrey, Thomas G.; Govindjee, Rajni; Honig, Barry; Pollock, Ernest Ferguson; Chan, Wan; Crouch, Rosalie K.; Yudd, Anthony P.; Nakanishi, K.

doi:10.1021/bi00689a002

Cited by 66 publications

(23 citation statements)

References 26 publications

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“…(According to n-electron theory, the replacement of a cis by a trans bond as well as a deviation from planarity causes a blue shift of the.absorption maximum.) The absorption maximum of the 1 l-cis,lCmethyl retinal (which was especially synthesized to enforce a 12-s-tram conformation) is still blue shifted by 25 nm relative to the other 14-methyl isomers [6]. Second, a direct experimental proof for the existence of a stable 12-s-trans conformation cannot be given yet [5,19,20].…”

Section: Discussionmentioning

confidence: 99%

A second crystal form of 11‐cis, 12‐cis retinal, the chromophoric group in visual pigments

Drikos¹,

Rüppel²,

Dietrich³

et al. 1981

FEBS Letters

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Section: Discussionmentioning

confidence: 99%

A second crystal form of 11‐cis, 12‐cis retinal, the chromophoric group in visual pigments

Drikos¹,

Rüppel²,

Dietrich³

et al. 1981

FEBS Letters

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“…In or der to ex plore this as pect, 14-methylretinal 7/8 was pre pared by grad u ate stu dent Wan Kit Chan; this is one of the ear li est ret inal analogs to be syn the sized and in cor po rated into rho dopsin. 22,23 The all-trans forms of ret i nal and 14-methyl-retinal ab sorb at sim i lar wave length of 368 and 373 nm, re spectively. In con trast, 11-cis-ret i nal 5/6 ab sorbs at 363 nm, while the 14-methyl an a log 7/8 ab sorbs at blue-shifted 338 nm.…”

Section: The Chromo Phore Adopts 12-s-trans (This Was Er Rone Oumentioning

confidence: 99%

“…Since the 14-Me chromo phore can not be 12-s-cis-in clined as in 7 in the pigment, this im plied that the con for ma tion of the chromo phore in Rh must also be twisted to ward the 12-s-trans conformer. 22,23 The con for ma tion around the 6-s-bond was de termined much later in 2001 (see be low).…”

Section: The Chromo Phore Adopts 12-s-trans (This Was Er Rone Oumentioning

confidence: 99%

Bioorganic Studies on Rhodopsins

Nakanishi

Berova

Fishkin

et al. 2002

J Chinese Chemical Soc

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A sum mary of on go ing bioorganic stud ies on rho dop sin, the most in ten sively stud ied G-protein cou pled re cep tor (GPCR) is given. The ar ti cle in cludes: (i) gen eral de scrip tions of rho dop sin and (ii) var i ous nat u rally oc cur ring ret i nal chromo phores in an i mals, fish and mi cro or gan isms; (iii) the ra tio nale for 6-s-cis-11-sicis ret i nal be ing the com mon chromophoric struc ture in vi sual pig ments; (iv) elec tro static charge dis tri bu tion within the op sin bind ing site; (v) the vi sual transduction cy cle; and (vi) the changes oc cur r ing in the chromophore/re cep tor in ter ac tions allong the vi sual transduction path. I. Rho dop sin (Fig. 1)Rhodopsins (Rh), 1,2 the pig ment re spon si ble for vi sion in an i mals, fish, birds and in sects are the most thor oughly inves ti gated G-protein cou pled re cep tors (GPCR, guanyl nucle o tide bind ing pro tein or transducin), and con sist of seven hy dro pho bic transmembrane he li ces A, B, …G (or 1,2,…7) in ter con nected by extramembrane loops. (Fig. 1a). [3][4][5][6][7] The major ity of vi sual pig ment stud ies have been per formed with the readily ac ces si ble bo vine Rh, con tain ing 348 amino ac ids. 8,9 The over all struc ture of bo vine Rh was fi nally de ter mined in 2000 by X-ray crys tal log ra phy at 2.8 Å res o lu tion (Fig. 1b). 10 Al though fur ther res o lu tion is needed for clar i fi ca tion of the chromo phore con for ma tion in more de tail, it is the first success ful crys tal lo graphic study for any GPCR. In the fol lowing we will out line our past and on go ing struc tural and bioorganic stud ies. II. The ret i nal chromo phores of Rh, Chlamydomonas,bacteriorhodopsin, etc. (Fig. 2) Re ceived Feb ru ary 22, 2002.

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“…High performance liquid chromatography (HPLC) is the means of choice for isolation, identification and quantitative analysis of the various classes of vitamin A compounds and their geometric isomers. Therefore, it is also widely used in studies concerning the visual pigment chromophores and their conversion (Rotmans and Kropf, 1975;Ebrey et al, 1975;Pilkiewicz et al, 1977;Tsukida et al, 1977; Groenendijk et a!., Bridges et al, 1980;Denny et al, 1981). In general, silica-gel-based columns are used, which yield good resolution in separating geometric isomers of retinal and retinol from mixtures dissolved in organic solvents.…”

Section: Introductionmentioning

confidence: 99%

An Improved HPLC Method for the Separation of Retinaldehyde Isomers From Visual Pigments

Pepe

Schwemer

1987

Photochem & Photobiology

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Abstract— A method for the analytical separation of retinal isomers such as 13‐cis, 11‐cis, 9‐cis and all‐trans retinal, dissolved in aqueous solutions of detergents, is described. The retinals are extracted by means of a non‐isomerizing procedure and separated by HPLC on an octadecyl silane column used in normal phase. This column retains detergents without deteriorating and gives a satisfactory separation of retinal isomers with a resolution comparable with that obtained with silica gel column. The reliability of the method is verified by analysing the chromophore of visual pigment rhodopsin in digitonin solution, before and after irradiation with white light.

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Properties of several sterically modified retinal analogs and their photosensitive pigments

Cited by 66 publications

References 26 publications

A second crystal form of 11‐cis, 12‐cis retinal, the chromophoric group in visual pigments

A second crystal form of 11‐cis, 12‐cis retinal, the chromophoric group in visual pigments

Bioorganic Studies on Rhodopsins

An Improved HPLC Method for the Separation of Retinaldehyde Isomers From Visual Pigments

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