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Volumn 9, Issue 23, 2003, Pages 5821-5831

(9Z)- and (11Z)-8-Methylretinals for Artificial Visual Pigment Studies: Stereoselective Synthesis, Structure, and Binding Models

Author keywords

Cross coupling; Docking models; Membrane proteins; Receptors

Indexed keywords

CHEMICAL BONDS; CHROMOPHORES; CRYSTAL STRUCTURE; IODINE; ISOMERS; PIGMENTS; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

EID: 0347624088     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.200304847     Document Type: Article
Times cited : (17)

References (69)
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    • The twisted polyene chain of 11-cis-retinal 1 within the binding pocket is intrinsically chiral. The absolute sense of twist around the 6-s-cis bond has been determined as negative with the use of locked synthetic retinal analogues; see: Y. Fujimoto, J. Ishihara, S. Maki, N. Fujioka, T. Wang, T. Furuta, N. Fishkin, B. Borham, N. Berova, K. Nakanishi, Chem. Eur. J. 2001, 7, 4198-4204. See also the discussion in the same paper on the positive helicity about the 12-s-bond.
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    • Substitution of the retinal side chain at C8 is uncommon. For previous studies on the interaction of a trans-retinal that was modified at C8 with bacteriorhodopsin, which is the protein of the purple membrane of Halobacterium salinarum; see: a) A. R. de Lera, B. Iglesias, J. Rodríguez, R. Alvarez, S. López, J. Villanueva, E. Padrós, J. Am. Chem. Soc. 1995, 117, 8220-8231;
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    • note
    • However, upon binding the apoproteins, a selection of 6-s-cis or 6-s-trans conformations is made by the receptor depending upon the tolerance of its binding pocket (i.e., 6-s-cis for 11-cis-retinal in rhodopsin ref. [6], and 6-s-trans for trans-retinal in bacteriorhodopsin ref. [34], which is the protein of the purple membrane of Halobacterium salinarium).
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.