PMID: 11325261Apr 28, 2001Paper

Synthesis and characterization of photoswitchable lipids containing hemithioindigo chromophores

The Journal of Organic Chemistry
K EggersP J Montoya-Pelaez

Abstract

The synthesis of four lipids containing the hemithioindigo chromophore as part of the fatty acid is described. Heck reaction of bromophenyl thioacetate esters with acrylonitrile, followed by reduction, ester hydrolysis, and Friedel--Craft acylation--cyclization gave a substituted thioindoxyl that condensed with an alkoxy benzaldehyde to produce the hemithioindigo. "Solventless" nitrile hydrolysis followed by mixed anhydride coupling of the acid with glycerophosphocholine produced lipids bearing two hemithioindigo chromophores. The photochemistry of various hemithioindigo derivatives was studied to confirm the expected photoisomerization in both homogeneous organic solution, and in vesicle bilayer membranes. Characteristic changes in the UV--visible spectra are consistent with fully reversible Z--E photoisomerization. Chromatographic separation of the Z and E isomers of a compound containing a single hemithioindigo chromophore confirmed the spectroscopic analysis and provided a quantitative analysis of the compositions of Z--E isomer mixtures.

References

Jan 28, 1992·Biochemistry·H LamparskiD F O'Brien
Jan 6, 1999·Biophysical Journal·B J RavooJ B Engberts

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Citations

Jul 13, 2011·Journal of Fluorescence·Natasha ShankerSusan L Bane
May 20, 2008·Free Radical Biology & Medicine·E VendittiE Damiani
Sep 29, 2015·Nature Communications·Manuel GuentnerHenry Dube
Aug 30, 2016·Journal of the American Chemical Society·Sandra WiedbraukHenry Dube
Mar 18, 2017·The Journal of Physical Chemistry Letters·Sandra WiedbraukHenry Dube
Nov 3, 2016·Chemistry : a European Journal·Manuel GuentnerHenry Dube
Sep 30, 2004·Organic & Biomolecular Chemistry·Tyler LougheedG Andrew Woolley
Jul 28, 2017·Journal of the American Chemical Society·Joshua E Zweig, Timothy R Newhouse
Oct 13, 2010·Organic & Biomolecular Chemistry·Anshuman MangalumRhett C Smith
Oct 25, 2001·Proceedings. Biological Sciences·R Ferrer I Cancho, R V Solé
Sep 26, 2001·Proceedings. Biological Sciences·R V Solé, J M Montoya
Sep 12, 2017·Angewandte Chemie·Ludwig Alexander HuberHenry Dube
Feb 23, 2020·Beilstein Journal of Organic Chemistry·Alexander SailerOliver Thorn-Seshold
Apr 24, 2008·The Journal of Organic Chemistry·Kiyoshi TanakaTakayuki Irie
Jun 10, 2004·Chemical Reviews·Jürgen-Hinrich Fuhrhop, Tianyu Wang
Sep 26, 2017·Journal of the American Chemical Society·Christian PetermayerHenry Dube
Jun 2, 2020·The Journal of Organic Chemistry·Bedřich FormánekJan Veselý
Apr 26, 2018·Accounts of Chemical Research·Christian Petermayer, Henry Dube
Dec 16, 2017·Organic Letters·Aaron GerwienHenry Dube

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