The crystal structure of 13-cis-retinal. The molecular structures of its 6-s-cis and 6-s-trans conformers

Simmons, Charles J.; Liu, R. S. H.; Denny, Marlene; Seff, K.

doi:10.1107/s0567740881008388

Cited by 53 publications

(32 citation statements)

References 8 publications

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“…The crystal structure consists of the linear molecules alternating oriented and held together by van der Waals forces. Other isomers of retinal, such as the 13-cis and 9-cis retinal, also form van der Waals www.lpr-journal.org bonded crystals [237,238]. The arrows superimposed on the chemical structure of all-trans retinal in Fig.…”

Section: Static Thz-tds Of Solid-state Materialsmentioning

confidence: 99%

Terahertz spectroscopy and imaging – Modern techniques and applications

Jepsen

Cooke

Koch

2010

Laser & Photonics Reviews

1,746

977

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Over the past three decades a new spectroscopic technique with unique possibilities has emerged. Based on coherent and time-resolved detection of the electric field of ultrashort radiation bursts in the far-infrared, this technique has become known as terahertz time-domain spectroscopy (THz-TDS). In this review article the authors describe the technique in its various implementations for static and time-resolved spectroscopy, and illustrate the performance of the technique with recent examples from solid-state physics and physical chemistry as well as aqueous chemistry. Examples from other fields of research, where THz spectroscopic techniques have proven to be useful research tools, and the potential for industrial applications of THz spectroscopic and imaging techniques are discussed.

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Section: Static Thz-tds Of Solid-state Materialsmentioning

confidence: 99%

Terahertz spectroscopy and imaging – Modern techniques and applications

Jepsen

Cooke

Koch

2010

Laser & Photonics Reviews

1,746

977

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“…The crystallographic data has shown that the retinal adopts an almost planar geometry in its isolated form;86-88 the protein environment induces non-planarity due to steric and electrostatic interactions 24,89-93. solid-state NMR measurements of the H-C 14 -C 15 -H bond along the photocycle indicated that the retinal twist increases by ~17° from the bR resting state to early-M 93.…”

Section: Resultsmentioning

confidence: 99%

Long-Distance Proton Transfer with a Break in the Bacteriorhodopsin Active Site

et al. 2009

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Bacteriorhodopsin is a proton-pumping membrane protein found in the plasma membrane of the archaeon Halobacterium salinarium. Light-induced isomerization of the retinal chromophore from all-trans to 13-cis leads to a sequence of five conformation-coupled proton transfer steps and the net transport of one proton from the cytoplasmic to the extracellular side of the membrane. The mechanism of the long-distance proton transfer from the primary acceptor Asp85 to the extracellular proton release group during the O→bR is poorly understood. Experiments suggest that this long-distance transfer could involve a transient state [O] in which the proton resides on the intermediate carrier Asp212.1 To assess whether the transient protonation of Asp212 participates in the deprotonation of Asp85, we performed hybrid Quantum Mechanics/Molecular Mechanics proton transfer calculations using different protein structures, and with different retinal geometries and active site water molecules. The structural models were assessed by computing UV-Vis excitation energies and C=O vibrational frequencies. The results indicate that a transient [O] conformer with protonated Asp212 could indeed be sampled during the long-distance proton transfer to the proton release group. Our calculations suggest that in the starting proton transfer state O, the retinal is strongly twisted, and at least three water molecules are present in the active site.

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“…e X-ray diffraction of bromine and mercury-labelled retinal derivatives . within the range found in small molecule crystal structures of various retinals and retinal derivatives (Hamanaka et al, 1972;Stam, 1972;Simmons et al, 1981Simmons et al, , 1986. The angle between the polyene chain of the retinal in the refined model and the membrane normal (70.7°), the orientation of methyl groups C 16 , C 17 ; C 18 , C 19 and C 20 and the position of some atoms of the retinal within the unit cell of purple membrane (PM) have been estimated also by other methods, and the results are summarised and compared with the refined model in Table 4.…”

Section: Structural Detailsmentioning

confidence: 95%