Isomers, visual pigment, and bacteriorhodopsin analogs of 3,7,13-trimethyl-10-isopropyl-2,4,6,8,10-tetradecapentaenal and 3,7,11-trimethyl-10-isopropyl-2,4,6,8,10-dodecapentaenal (two ring open retinal analogs)

Six geometric isomers of 2 (3,7,13-trimethyl-10-isopropyl-2,4,6,8,10-tetradecapentaenal) have been isolated and characterized. Of these, four (equivalent to 9- cis, 11- cis, 5,9- dicis, and 5,11- dicis of retinoids) were found to form stable visual pigment analogs. So were four isomers (equivalent t...

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Published inBioorganic chemistry Vol. 17; no. 2; pp. 217 - 223
Main Authors Zhang, B.-W., Asato, A.E., Denny, M., Mirzadegan, T., Trehan, A., Liu, R.S.H.
Format Journal Article
LanguageEnglish
Published Elsevier Inc 01.06.1989
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Summary:Six geometric isomers of 2 (3,7,13-trimethyl-10-isopropyl-2,4,6,8,10-tetradecapentaenal) have been isolated and characterized. Of these, four (equivalent to 9- cis, 11- cis, 5,9- dicis, and 5,11- dicis of retinoids) were found to form stable visual pigment analogs. So were four isomers (equivalent to 7- cis, 9- cis, 11- cis, and 9,13- dicis) of 3 (3,7,11-trimethyl-10-isopropyl-2,4,6,8,10-dodecapentaenal). These analogs suggest that the hydrophobic pocket is more flexible than what was recognized earlier, perhaps capable of accepting analogs with 6- S-trans as well as a 6- S-cis conformers. The presence of bacteriorhodopsin analogs from isomers of 2 was also reported.
ISSN:0045-2068
1090-2120
DOI:10.1016/0045-2068(89)90021-7